Appendix II-B:
NMR spectra chapter 3
1.07
4.04
1.01
0.990.99
1.00
0.52 2.05 Acetone-d6
7.017.027.027.037.047.047.047.067.067.077.197.207.227.227.257.267.267.277.277.297.297.597.597.607.967.977.978.018.02
8.688.688.688.698.708.70
9.19
N-Phenylpyridine-2-sulfonamide (2)
1 H NMR (acetone-d 6 , 300 MHz)
13 C NMR (acetone-d 6 , 75 MHz)
158.0253 150.9340 139.0909 138.6244 129.8205 127.8964 125.2800 123.4871 121.9202
( p p m )
1 0 5 1 1 0 1 1 5 1 2 0 1 2 5 1 3 0 1 3 5 1 4 0 1 4 5 1 5 0 1 5 5 1 6 0 1 6 5
N-(2-Methoxyphenyl)pyridine-2-sulfonamide (24)
1 H NMR (CDCl 3 , 300 MHz)
N-(2-Fluorophenyl)pyridine-2-sulfonamide (25).
1 H NMR (CDCl 3 , 300 MHz)
N-(3-Methoxyphenyl)pyridine-2-sulfonamide (26)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
55.33
76.5977.0277.44
108.09111.51114.59
123.24
127.00
129.87
137.32138.07
150.07
156.17
160.20
N-(3-Bromophenyl)pyridine-2-sulfonamide (27)
1 H NMR (CDCl 3 , 300 MHz)
N-(2-Naphthyl)pyridine-2-sulfonamide (28)
1 H NMR (DMSO-d 6 , 300 MHz)
13 C NMR (DMSO-d 6 , 75 MHz)
N-(4-Chlorophenyl)pyridine-2-sulfonamide (29)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl 4-[N-(2-pyridyl)sulfonylamino]benzoate (30)
1 H NMR (DMSO-d 6 , 300 MHz)
13 C NMR (DMSO-d 6 , 300 MHz)
0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0
f1 (ppm)
4-Methyl-N-phenylbenzenesulfonamide (10) 1. 1 H NMR (acetone-d 6 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl (E)-3-(N-phenylpyridine-2-sulfonamido)acrylate (3)
1 H NMR (CDCl 3 , 300 MHz)
(E)-N-Phenyl-N-(2-pyridyl)sulfonylbut-2-enamide (4)
1 H NMR (CDCl 3 , 300 MHz)
N-(But-3-en-1-yl)-N-phenylpyridine-2-sulfonamide (5)
1 H NMR (CDCl 3 , 300 MHz)
N-(Cyanomethyl)-N-phenylpyridine-2-sulfonamide (7)
1 H NMR (CDCl 3 , 300 MHz)
Methyl N-phenyl-N-[(2-pyridyl)sulfonyl]glycinate (6)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl N-(2-methoxyphenyl)-N-[(2-pyridyl)sulfonyl]glycinate (31)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl N-(2-fluorophenyl)-N-[(2-pyridyl)sulfonyl]glycinate (32)
1 H NMR (CDCl 3 , 500 MHz)
13 C NMR (CDCl 3 , 75 MHz)
19 F NMR (CDCl 3 , 282 MHz)
Methyl N-(3-methoxyphenyl)-N-[(2-pyridyl)sulfonyl]glycinate (33)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl N-(3-bromophenyl)- N-[(2-pyridyl)sulfonyl]glycinate (34)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl N-2-naphthyl-N-[(2-pyridyl)sulfonyl]glycinate (35)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl N-(4-chlorophenyl)-N-[(2-pyridyl)sulfonyl]glycinate (36)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl 4-[N-(methoxycarbonyl)methyl-N-(2-pyridyl)sulfonyl]aminobenzoate (37)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Ethyl N-phenyl-N-tosylglycinate (11).
1 H NMR (CDCl 3 , 300 MHz)
N-Benzyl-N-phenylpyridine-2-sulfonamide (52)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.5959 150.1265 138.7734 137.8497 136.4387 129.2384 129.0348 128.6348 128.3948 128.0166 127.6529 126.7729 123.2309 56.9593
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
N S O O
N
N-Benzyl-N-methylpyridine-2-sulfonamide (58)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
150.0174 137.9079 128.6275 128.3293 127.8493 126.4892 122.8237 55.0029 35.0603
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
N-Benzyl-N-methyl-4-methylbenzenesulfonamide (59)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
143.5154 135.7551 134.3877 129.7985 128.6639 128.4093 127.9075 127.5511 54.1810 34.3766 21.5616
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
N-Methyl-N-(2-phenethyl)pyridine-2-sulfonamide (68)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3511 149.9683 138.3802 137.8846 128.8547 128.5705 126.5299 126.4643 122.6380 52.6654 36.0705 35.2105
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
N-Methyl-N-(2-phenethyl)-4-methylbenzenesulfonamide (69)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
143.2778 138.3657 134.8747 129.6710 128.8183 128.5997 127.3898 126.5663 51.8491 35.1813 34.8606 21.4943
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
N-Methyl-N-[2-(4-methylphenyl)ethyl]pyridine-2-sulfonamide (97)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.4094 149.9464 137.8263 136.0262 135.2464 129.2410 128.7163 126.3914 122.6307 52.7455 36.0486 34.7222 21.0279
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
Me
N-Methyl-N-[2-(4-clorophenyl)ethyl]pyridine-2-sulfonamide (98)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3073 149.9537 137.8701 136.8352 132.3384 130.2249 128.6653 126.4570 122.6089 52.4540 36.0413 34.5400
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
Cl
N-Methyl-N-[2-(3-methylphenyl)ethyl]pyridine-2-sulfonamide (99)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3656 149.9683 138.2782 138.1397 137.8774 129.6491 128.4612 127.2732 126.4497 125.8375 122.6235 52.7091 36.0340 35.1230 21.3559
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
Me
N-Methyl-N-[2-(3-clorophenyl)ethyl]pyridine-2-sulfonamide (100)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.2563 149.9828 140.4136 137.9065 134.2479 129.8386 128.9349 127.1056 126.7485 126.5226 122.6162 52.3666 36.0705 34.8752
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
Cl
N-Methyl-N-[2-(2-methoxyphenyl)ethyl)pyridine-2-sulfonamide (101)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.5405 149.9245 137.7826 130.6476 127.9073 126.6829 126.3258 122.6016 120.5536 110.2848 55.2672 50.8725 35.8883 29.8756
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
OMe
N-Methyl-N-[2-(2-methylphenyl)ethyl)pyridine-2-sulfonamide (102)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.4531 149.9610 137.8628 136.5072 136.2886 130.4144 129.5398 126.7485 126.4424 126.1654 122.6307 51.5649 36.0777 32.7107 19.2569
( p p m )
2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0
Me N S O O
N
Me
N-Methyl-N-[2-(2-clorophenyl)ethyl]pyridine-2-sulfonamide (103)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3438 149.9828 137.8701 135.9387 133.9855 131.3035 129.5252 128.1770 127.0619 126.4643 122.6453 50.7122 36.0777 33.0459
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
Cl
N-Methyl-N-(2-(naphthalen-2-yl)ethyl)pyridine-2-sulfonamide (104)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.7684 8.7542 8.0409 8.0149 7.9638 7.9382 7.9331 7.9123 7.8539 7.8239 7.7911 7.7480 7.5387 7.5160 7.5007 7.4879 7.4821 7.4689 4.6139 2.8341
( p p m )
2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
157.3219 150.0484 137.9575 133.4827 133.2567 133.0527 128.5705 127.7761 127.7397 127.2441 126.5663 126.2966 126.1290 126.1071 122.8494 55.2308 35.0939
( p p m )
3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0
N-Methyl-N-(3-phenylpropyl)pyridine-2-sulfonamide (71)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.2126 149.9828 141.4339 137.8774 128.4320 128.3737 126.4715 125.9760 122.7328 50.6466 35.4947 32.7544 29.6351
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
N-Methyl-N-(4-phenylbutyl)pyridine-2-sulfonamide (73)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3146 149.9391 142.0680 137.8118 128.4393 128.3227 126.3841 125.7865 122.6963 50.6976 35.3635 35.3198 28.1046 27.2665
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N S O O
N
Methyl (E)-3-{2-[N-(methoxycarbonyl)methyl-N-(2-pyridyl)sulfonyl- amino]phenyl}acrylate (8)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl N-{[2-(E)-(phenylsulfonyl)vinyl]phenyl}-N-[(2-pyridyl)sulfonyl]glycinate (13)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
(E)-Methyl N-{2-[(Z)-cyanovinyl]phenyl}-N-[(2-pyridyl)sulfonyl]-glycinate (E-14).
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
(Z)-Methyl N-{2-[(Z)-cyanovinyl]phenyl}-N-[(2-pyridyl)sulfonyl]-glycinate (Z-14).
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl N-{[2-(E)-(dimethoxyphosphoryl)vinyl]phenyl}-N-[(2-pyridyl)sulfonyl]- glycinate (15)
1 H NMR (acetone-d 6 , 300 MHz)
13 C NMR (acetone-d 6 , 75 MHz)
Methyl (E)-3-{5-chloro-2-[N-(methoxycarbonyl)methyl-N-(2-pyridyl)sulfonyl- amino]phenyl}acrylate (38)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
51.7452.2654.16
76.5877.0077.42
121.13122.81127.02127.04130.49132.37135.18136.40136.73137.95138.72
150.32
156.88
166.22168.68
N SO 2 Py MeO 2 C
CO 2 Me
Cl
Methyl 3-[(E)-2-(methoxycarbonyl)vinyl]-4-[N-(methoxycarbonyl)methyl-N-(2- pyridyl)sulfonylamino]benzoate (39)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl (E)-3-{4-methoxy-2-[N-(methoxycarbonyl)methyl-N-(2-pyridyl)sulfonyl- amino]phenyl}acrylate (40)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
N SO 2 Py MeO 2 C
CO 2 Me
MeO
Methyl (E)-3-{3-[N-(methoxycarbonyl)methyl-N-(2-pyridyl)sulfonylamino]-2- naphthyl}acrylate (41)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl (E)-3-(4-bromo-2-[N-(methoxycarbonyl)methyl-N-(2-pyridyl)sulfonyl- amino]phenyl}acrylate (42)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Butyl (2E)-3-{2-[{2-[(1E)-3-butoxy-3-oxoprop-1-en-1-yl]benzyl}(pyridin-2- ylsulfonyl)amino]phenyl}acrylate (53)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
7.5298 7.5254 7.5188 7.4935 7.4389 7.4235 7.4176 7.3982 7.3927 7.3289 7.3032 7.2904 7.2285 7.2065 7.1889 7.1838 7.1647 7.1581 7.1387 7.1332 6.8704 6.8458 6.8407 6.0017 5.9658 5.9482 5.9138 5.4498 5.4036 4.9264 4.8791 4.1611 4.1395 4.1219 4.0999 1.7047 1.6801 1.6560 1.6310 1.6076 1.4863 1.4602 1.4514 1.4346 1.4258 1.4104 1.4005 1.3767 0.9948 0.9794 0.9552
( p p m )
1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
Butyl (E)-3-(2-{[N-methyl-N-(2-pyridyl)sulfonylamino]methyl}phenyl)acrylate (60)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
166.3737 166.0749 157.8466 150.3982 140.4938 139.4516 137.8919 137.1486 136.4853 134.4884 134.1386 132.1854 130.5529 130.2176 130.1010 129.0151 128.6798 127.0983 126.7922 126.3768 123.1701 120.2111 64.2825 54.1521 30.7429 19.2059 13.7398
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
N-Methyl-2-[2-(E)-(phenylsulfonyl)vinyl]-N-[(2-pyridyl)sulfonyl]benzylamine (63)
1 H NMR (CDCl 3 , 300 MHz)
166.8693 157.0085 150.1432 140.8509 138.0304 134.8091 133.8033 130.2613 129.5544 128.3008 126.9088 126.6829 122.9295 120.8670 64.6178 52.0386 35.2906 19.2132 13.7909
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
13 C NMR (CDCl 3 , 75 MHz)
Phenyl (E)-2-(2-{[N-methyl-N-(2-pyridyl)sulfonylamino]methyl}phenyl)ethene- sulfonate (64)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Dimethyl (E)-2-{2-[N-methyl-N-(2-pyridylsulfonyl)aminomethyl]phenyl}vinyl- phosphonate (65)
1 H NMR (acetone-d 6 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Butyl (E)-3-(2-{2-[N-methyl-N-(2-pyridyl)sulfonylamino]ethyl}phenyl)acrylate (74)
1 H NMR (CDCl 3 , 300 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
13 C NMR (CDCl 3 , 75 MHz)
Butyl (2E)-3-(2-{3-[N-methyl-N-(2-pyridyl)sulfonylamino]propyl}phenyl)acrylate (76)
1 H NMR (CDCl 3 , 300 MHz)
166.8765 157.3875 149.9828 141.2444 137.8774 137.7608 133.2932 130.7934 130.2540 127.3097 126.6975 126.4424 122.6599 120.3131 64.5085 52.2718 36.2308 32.6232 30.7502 19.1986 13.7326
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
13 C NMR (CDCl 3 , 75 MHz)
Methyl (E)-3-(2-(2-(N-methylpyridine-2-sulfonamido)ethyl)phenyl)acrylate (78)
1 H NMR (CDCl 3 , 300 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.9859 157.2272 149.9683 141.7255 141.0477 137.8263 132.9652 130.1666 130.0937 126.7339 126.6975 126.4132 122.7619 119.8248 64.4647 50.6174 35.3854 30.7793 30.2983 29.5112 19.2132 13.7471
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
N
CO 2 Bu Me
SO 2 Py
13 C NMR (CDCl 3 , 75 MHz)
(E)-3-{2-[2-N-Methyl-N-(2-pyridylsulfonylamino)ethyl]phenyl}acrylonitrile (79)
1 H NMR (CDCl 3 , 300 MHz)
8.6578 8.6431 7.9934 7.9415 7.9189 7.8904 7.8853 7.8652 7.8601 7.8396 7.8341 7.5474 7.5226 7.4601 7.4565 7.4404 7.4360 7.4200 7.3064 7.2874 7.2834 7.2615 7.2454 7.2154 6.3794 6.3268 3.7903 3.4550 3.4305 3.4035 3.0711 3.0437 3.0193 2.9349
( p p m )
3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
167.2264 157.4094 149.9901 141.6161 137.8628 137.8336 133.2422 130.8007 130.3269 127.3315 126.7193 126.4278 122.6672 119.8321 52.2791 51.7398 36.2599 32.6451
( p p m )
3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0
Me N
CO 2 Me
SO 2 Py
13 C NMR (CDCl 3 , 75 MHz)
N-Methyl-2-{[(E)-2-(phenylsulfonyl)vinyl]phenyl}-N-[(2-pyridyl)sulfonyl]- ethanamine (80)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3000 150.0338 147.7308 137.9940 137.5640 132.6154 131.2088 130.9246 127.5648 126.6027 126.0197 122.7473 118.0903 98.3542 52.2354 36.2964 32.6378
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Phenyl (E)-2-{2-[2-(N-methyl-N-(2-pyridylsulfonyl)amino)ethyl]phenyl}vinyl- sulfonate (81)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3073 150.0776 140.5302 139.3058 138.4385 137.9940 133.4389 131.2234 131.0630 129.4086 129.2847 127.7907 127.4700 127.1712 126.5444 122.7619 52.3738 36.2308 32.4920
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Dimethyl (E)-2-{2-[2-(N-methyl-N-(2-pyridylsulfonyl)amino)ethyl]phenyl}vinyl- phosphonate (82)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3000 150.0120 149.5674 143.2924 138.6135 137.9430 131.7481 131.2015 130.6185 129.8824 127.6376 127.2878 127.1056 126.5371 122.7182 122.5068 52.1479 36.0705 32.4264
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Dibutyl (E,E)-3,3'-(2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}-1,3- phenylene)bisacrylate (83)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.3511 149.9901 146.3024 146.2222 137.8992 137.4182 134.0220 133.7305 130.7934 130.3707 127.3461 126.4497 125.1597 122.6963 116.3922 113.8559 52.5925 52.5196 52.2937 36.2089 32.4847
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.5897 8.0064 7.9542 7.9381 7.9118 7.8479 7.8428 7.8223 7.8172 7.7968 7.7916 7.5053 7.4794 7.3986 7.3826 7.3771 7.3610 7.2376 7.2116 7.1952 6.3102 6.2580 4.1718 4.1495 4.1272 3.3131 3.2839 3.1031 3.0743 2.9716 1.6491 1.6265 1.6002 1.4011 1.3759 1.3507 1.3263 0.9062 0.8818 0.8573
( p p m )
1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
166.5777 157.6134 149.9828 141.3829 137.9357 136.3760 135.0423 128.4903 127.4919 126.3987 122.7036 121.9457 64.6324 51.3608 36.2381 30.7283 28.1483 19.1986 13.7326
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0
Dimethyl (E,E)-3,3'-(2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}-1,3- phenylene)bisacrylate (84)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.9203 157.5843 149.9901 141.7546 137.9284 136.5145 135.0059 128.5559 127.5429 126.4132 122.7036 121.4646 51.8345 51.4191 36.2891 28.2139
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
2-{2,6-Bis[(E)-2-(phenylsulfonyl)vinyl]phenyl}-N-[methyl-N-(2-pyridyl)sulfonyl]- ethanamine (85)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.0282 8.0121 8.0026 7.9996 7.9824 7.9758 7.9707 7.9556 7.9498 7.9300 7.9245 7.9040 7.6338 7.6294 7.6196 7.6097 7.6012 7.5902 7.5855 7.5807 7.5587 7.5386 7.5331 7.5151 7.5096 7.5048 7.4931 7.4839 7.4678 7.4634 7.4583 7.2688 7.2600 7.2431 7.2171 6.8557 6.8052 3.3925 3.3709 3.3573 3.3408 3.2089 3.1917 3.1799 3.1576 3.0586
( p p m )
3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
150.1942 140.1585 139.0580 138.1470 137.4984 133.6066 133.2713 131.3764 129.7220 129.4815 127.9219 127.7688 126.6392 122.8712 51.4993 36.2308 34.2120
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Diphenyl (E,E)-2,2'-(2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}-1,3- phenylene)divinylsulfonate (86)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
157.2417 150.0338 149.4800 143.0009 138.1179 137.7243 132.9506 130.1229 129.9917 128.1551 127.4117 126.6246 124.7370 122.7401 122.4340 51.2515 35.9684 28.0244
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Methyl (E,E)-3-(3-[(E)-2-(Phenylsulfonyl)vinyl]phenyl]-2-{2-[methyl(2- pyridylsulfonyl)amino]ethyl}phenyl)acrylate (87)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.7422 8.7269 8.1250 8.1019 8.0746 8.0501 8.0318 7.9778 7.9726 7.9518 7.9471 7.9263 7.6483 7.6206 7.6016 7.5767 7.5534 7.5271 7.5110 7.4862 7.3276 7.3017 7.2758 6.8941 6.8437 6.4094 6.3572 3.8451 3.4383 3.4156 3.3864 3.2294 3.2001 3.1775 3.0814
( p p m )
1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
166.7792 157.4475 150.0832 141.3425 139.4528 138.0297 136.9955 135.2846 133.4961 132.9595 130.9687 129.4057 129.3590 128.8924 127.9281 127.8037 127.6404 126.5051 122.7801 121.8236 51.8591 51.4314 36.2362 28.1021
( p p m )
2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0
Methyl (E,E)-3-(3-[(E)-2-Cyanovinyl]-2-{2-[methyl(2- pyridylsulfonyl)amino]ethyl}phenyl)acrilatate (88)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.6244 8.6094 7.9936 7.9410 7.9290 7.9027 7.8709 7.8658 7.8461 7.8410 7.8161 7.7617 7.5469 7.5210 7.4301 7.4085 7.3888 7.2748 7.2489 7.2230 7.1927 6.3249 6.2723 5.7916 5.7372 3.7500 3.3559 3.3332 3.3040 3.1126 3.0849 3.0608 2.9223
( p p m )
1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
166.7948 157.4008 149.9977 147.9913 141.2725 137.9908 136.2178 135.1602 134.3981 129.3435 127.8815 127.7571 126.5595 122.7490 121.8625 117.6632 100.0419 51.8746 51.3769 36.3062 28.4676
( p p m )
2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0
Butyl (E)-3-(5-methyl-2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}phenyl) acrylate (105)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.9786 157.4385 149.9755 141.3902 137.8336 136.8497 134.8310 133.0235 131.1578 130.7423 127.2076 126.3768 122.6526 119.9487 64.4720 52.3738 36.2235 32.1568 30.7647 21.0060 19.2132 13.7398
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Me N
CO 2 Bu
Me
SO 2 Py
Me N
CO 2 Bu
Cl
SO 2 Py
Butyl (E)-3-(5-chloro-2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}phenyl) acrylate (106).
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.5199 157.3486 149.9956 139.9443 137.8933 136.1478 134.9987 133.1731 132.1549 130.0457 126.5911 126.4674 122.6564 121.6018 64.6978 52.1082 36.2676 32.1147 30.7256 19.1979 13.7359
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Butyl (E)-3-(4-methyl-2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}phenyl) acrylate (107)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
167.1025 157.4312 149.9828 141.1060 140.6468 137.8555 137.7097 131.5367 130.3488 128.1697 126.6100 126.4060 122.6672 119.1252 64.4356 52.3738 36.1944 32.5940 30.7793 19.2132 13.7398
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Butyl (E)-3-(4-chloro-2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}phenyl) acrylate (108).
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.6360 157.3146 150.0047 139.9836 139.4880 137.9211 135.9460 131.8793 130.5966 128.0166 127.5720 126.5153 122.6672 120.8087 64.6178 52.0022 36.2235 32.4629 30.7210 19.1840 13.7253
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Butyl (E,E)-3-(3-{2-[methyl(2-pyridylsulfonyl)amino]ethyl}-2-naphthyl)acrylate (109)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
7.8404 7.8352 7.8152 7.7976 7.7907 7.7753 7.7465 7.7012 7.5098 7.4919 7.4861 7.4802 7.4707 7.4605 7.4496 7.4404 7.4251 7.4152 7.3999 6.5390 6.4872 4.2585 4.2366 4.2143 3.5627 3.5386 3.5112 3.2329 3.2055 3.1814 2.9904 1.7336 1.7106 1.6847 1.4900 1.4652 1.4400 1.4155 0.9951 0.9707 0.9462
( p p m )
1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0
166.8326 157.4286 149.9665 141.7553 137.8206 134.5405 134.1332 132.2713 131.9295 129.1875 128.1039 127.3402 127.2165 126.7220 126.3947 126.3074 122.6127 120.9254 64.5960 52.2100 36.2894 32.9439 30.7983 19.2415 13.7722
( p p m )
0 2 0 4 0
6 0 8 0 1 0 0 1 2 0 1 4 0
1 6 0 1 8 0 2 0 0
Butyl (E)-3-(3-methoxy-2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}phenyl) acrylate (110)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.8401 157.9414 157.6936 149.9172 141.6307 137.8118 134.9840 127.7105 126.4788 126.2748 122.6162 120.9691 118.8555 111.5164 64.4939 55.6826 50.5373 35.8810 30.7502 24.8031 19.2132 13.7471
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Butyl (E)-3-(3-methyl-2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}phenyl) acrylate (111)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.9276 157.4822 149.9828 142.0680 137.8774 137.7170 135.8586 133.8106 132.2510 126.9598 126.4351 124.6787 122.6453 120.6119 64.4866 50.8434 36.1215 30.7575 28.6949 19.9493 19.2059 13.7326
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Butyl (E)-3-(3-chloro-2-{2-[N-methyl-N-(2-pyridylsulfonyl)amino]ethyl}phenyl) acrylate (112)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
166.4471 157.5959 149.9883 141.0862 137.9151 136.2496 135.5078 135.0714 130.8385 128.0893 126.4311 125.5292 122.7000 122.2782 64.6905 50.0500 36.1294 30.7183 29.0528 19.2052 13.7504
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Butyl (2-methylisoindol-1-yl)acetate (113)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
172.1128 142.6245 139.2651 127.1806 126.9006 122.0792 77.3803 76.9448 76.5249 67.0532 64.4558 60.5054 40.7377 39.6801 30.5817 19.0726 13.6291
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Butyl (2-methyl-1,2,3,4-tetrahydroisoquinol-1-yl)acetate (114)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
( p p m )
0 . 5 1 . 0 1 . 5 2 . 0 2 . 5 3 . 0 3 . 5 4 . 0 4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5
172.3426 137.3891 134.1459 128.9641 127.2878 126.3112 125.9541 64.3773 60.0263 46.3466 42.2945 40.9535 30.6627 25.1384 19.1330 13.7034
( p p m )
1 0 2 0 3 0 4 0 5 0 6 0 7 0 8 0 9 0 1 0 0 1 1 0 1 2 0 1 3 0 1 4 0 1 5 0 1 6 0 1 7 0 1 8 0 1 9 0
Methyl 3-[(methoxycarbonyl)methyl]-1H-indole-2-carboxylate (45)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
30.49
51.8452.08
76.6777.1077.52
112.07115.82120.48120.62124.17125.74127.81
135.92
162.36
171.93
Methyl 3-methyl-1H-indole-2-carboxylate (47)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl 3-methyl-1H-indole-2-carboxylate (47)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
Methyl 5-chloro-3-[(methoxycarbonyl)methyl]-1H-indole-2-carboxylate (48)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
9.89
51.65
76.5877.0077.42
111.60
119.95120.38120.80123.20125.65128.52
135.90
163.01
Dimethyl 3-[(methoxycarbonyl)methyl]-1H-indole-2,5-dicarboxylate (49)
1 H NMR (CDCl 3 , 300 MHz)
30.25
51.9952.20
76.6277.0477.46
113.21115.10119.75
125.40126.18126.42128.70
134.07
161.92
171.74
13 C NMR (CDCl 3 , 75 MHz)
Dimethyl 3-[(methoxycarbonyl)methyl]-1H-indole-2,5-dicarboxylate (49)
1 H NMR (CDCl 3 , 300 MHz)
30.22
52.0152.20
76.6277.0477.47
111.85
117.08
122.78123.67125.66126.51127.39
138.14
161.88
167.60
171.66