Appendix II-A:
NMR spectra chapter 2
N-(2-pyridylsulfonyl)indole (1)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.6363 8.6217 8.1702 8.1439 8.0563 8.0293 7.9394 7.9138 7.8879 7.7166 7.7046 7.5921 7.5669 7.4909 7.4748 7.4672 7.3320 7.3017 7.2929 7.2667 6.7305 6.7184
( 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 9 . 5 1 0 . 0
155.4051 150.4711 138.1470 134.9986 130.8225 127.6012 127.3461 124.5329 123.4834 122.2955 121.3772 113.6956 108.8855
( 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 1 8 0
N-(4-Toluensulfonyl)indole (5)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.0671 8.0400 7.8164 7.7889 7.6178 7.6057 7.5753 7.5496 7.3531 7.3271 7.2839 7.2582 7.2351 7.2091 6.6949 6.6828 2.3392
( p p m )
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
144.9468 135.3703 134.8820 130.7934 129.8824 126.8214 126.3768 124.5767 123.3085 121.4136 113.5717 109.0677 21.5308
( 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
N
O 2 S
N-(2-Thienylsulfonyl)indole (6)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.0390 8.0117 7.6818 7.6702 7.5610 7.5321 7.5211 7.3772 7.3524 7.3272 7.2841 7.2600 7.2348 7.0025 6.9875 6.9737 6.6917 6.6796
( p p m )
4 . 4 4 . 8 5 . 2 5 . 6 6 . 0 6 . 4 6 . 8 7 . 2 7 . 6 8 . 0 8 . 4 8 . 8 9 . 2 9 . 6 1 0 . 0
138.2636 134.7799 133.5264 133.1183 130.8954 127.4992 126.2092 124.8026 123.6802 121.5521 113.7320 109.8621
( 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
N SO 2
S
N-(8-Quinolylsulfonyl)indole (7)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.8606 8.8548 8.8464 8.8405 8.4154 8.4106 8.3905 8.3858 8.0242 8.0118 8.0023 7.9965 7.9745 7.9687 7.8971 7.8927 7.8697 7.8653 7.7850 7.7824 7.7554 7.5220 7.4968 7.4698 7.4077 7.4022 7.3847 7.3799 7.3281 7.3138 7.3003 7.2861 7.1641 7.1104 7.1053 7.0845 7.0808 7.0764 7.0563 7.0516 6.5016 6.4997 6.4891
( p p m )
4 . 5 5 . 0 5 . 5 6 . 0 6 . 5 7 . 0 7 . 5 8 . 0 8 . 5 9 . 0 9 . 5 1 0 . 0 1 0 . 5
151.4332 143.8609 136.2448 135.5598 134.8237 134.6706 131.9667 130.6039 129.5398 128.9568 125.1888 123.8041 122.8421 122.3757 121.1075 113.3312 106.2472
( 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 1 8 0
N-(4-Nitrophenylsulfonyl)indole (8)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.2652 8.2356 8.0431 8.0135 7.9947 7.9670 7.5487 7.5355 7.5236 7.3449 7.3198 7.2845 7.2537 6.7235 6.7121
( p p m )
5 . 4 5 . 6 5 . 8 6 . 0 6 . 2 6 . 4 6 . 6 6 . 8 7 . 0 7 . 2 7 . 4 7 . 6 7 . 8 8 . 0 8 . 2 8 . 4 8 . 6 8 . 8 9 . 0 9 . 2 9 . 4
150.6460 143.4163 134.7726 130.9173 128.0385 126.0124 125.2544 124.4965 124.1102 121.8145 113.4259 110.7148
( p p m )
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-(N’N’-Dimethylsulfonyl)indole (9)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
N-(2-Pyridylsulfonyl)-6-fluoroindole (27)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.6567 8.6432 8.1849 8.1586 7.9847 7.9796 7.9588 7.9537 7.9328 7.9277 7.7995 7.7926 7.7674 7.7604 7.6837 7.6713 7.5351 7.5325 7.5194 7.5022 7.4909 7.4734 7.3017 7.0632 7.0555 7.0333 7.0260 7.0037 6.9960 6.6962 6.6841
( p p m )
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
162.3871 159.1876 155.3468 150.5732 138.2053 135.3265 135.1589 127.6959 122.3028 122.0550 121.9238 112.0995 111.7715 108.4919 101.4371 101.0581
( p p m )
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
N-(2-Pyridylsulfonyl)-5-methoxyindole (28)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.6095 8.6066 8.6040 8.1243 8.1213 8.1180 8.0982 8.0950 8.0917 7.9260 7.9216 7.9157 7.8956 7.8897 7.8695 7.8637 7.6570 7.6445 7.4781 7.4744 7.4627 7.4590 7.4528 7.4491 7.4371 7.4334 7.2879 7.0123 7.0042 6.9448 6.9368 6.9151 6.9067 6.6417 6.6391 6.6292 6.6271 3.8353
( p p m )
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
156.5712 155.3323 150.4055 138.1397 131.8283 129.6419 128.0749 127.5648 122.2226 114.5191 113.6008 109.0094 103.7328 55.6389
( 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 1 8 0
N-(2-Pyridylsulfonil)-5-bromoindole (29)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.6180 8.6150 8.6125 8.6095 8.6022 8.5993 8.5967 8.5941 8.1411 8.1378 8.1177 8.1147 8.1114 7.9472 7.9414 7.9319 7.9212 7.9157 7.9022 7.8952 7.8897 7.6951 7.6888 7.6830 7.6705 7.5023 7.4986 7.4869 7.4832 7.4766 7.4730 7.4612 7.4576 7.4231 7.4169 7.3938 7.3876 7.2882 6.6476 6.6454 6.6351 6.6329
( p p m )
4 . 6 4 . 8 5 . 0 5 . 2 5 . 4 5 . 6 5 . 8 6 . 0 6 . 2 6 . 4 6 . 6 6 . 8 7 . 0 7 . 2 7 . 4 7 . 6 7 . 8 8 . 0 8 . 2 8 . 4 8 . 6 8 . 8 9 . 0 9 . 2 9 . 4
155.2885 150.5440 138.1980 133.8179 132.5279 128.5632 127.7470 127.4044 123.9790 122.2372 116.9606 115.2406 108.0765
( p p m )
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
N-(2-Pyridylsulfonyl)-6-methoxycarbonylindole (30)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.7071 8.6352 8.6213 8.2480 8.2217 7.9869 7.9595 7.8726 7.8602 7.6341 7.6067 6.7754 6.7634 3.9839
( p p m )
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
167.1826 155.3031 150.5513 138.2855 134.5540 134.5103 130.4363 127.7542 126.4788 124.6422 122.3611 121.0638 115.4156 108.5721 52.1844
( 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 1 8 0
7-Aza-N-(2-pyridylsulfonyl)indole (31)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
N-(2-Pyridylsulfonyl)-7-methylindole (32)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
8.6026 8.5996 8.5872 8.5842 8.0015 7.9780 7.9751 7.8952 7.8897 7.8076 7.7951 7.4781 7.4740 7.4623 7.4583 7.4528 7.4139 7.3886 7.2545 7.1497 7.1248 7.0995 7.0306 7.0064 6.7084 6.6959 2.5649
( p p m )
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
N-(2-Pyridylsulfonyl)-7-methylindole (32)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
157.0085 150.3108 138.2418 134.8965 132.8850 130.0208 128.2498 127.3971 124.5694 123.8114 121.9675 119.4021 108.7543 21.9389
( 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 1 8 0
tert-Butyl-1-indole carboxylate (10)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
N,N’-Bis(2-pyridylsulfonyl)-2,2’-biindole (2)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
149.8152 135.2026 130.5820 125.8812 124.1758 122.6162 120.9180 115.1605 107.2675 83.6178 28.2212
( 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
6,6’-Difluoro-N,N’-bis(2-pyridylsulfonyl)-2,2’-biindole (34)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
155.9231 150.1411 137.7697 137.6388 130.7730 128.8312 127.3620 125.4128 123.7255 122.5764 121.1654 115.5506 115.4197
( 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 1 8 0
5,5’-Dimethoxy-N,N’-bis(2-pyridylsulfonyl)-2,2’-biindole (35)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
5,5’-Dibromo-N,N’-bis(2-pyridylsulfonyl)-2,2’-biindole (38)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
N,N’-Bis(2-pyridylsulfonyl)-2,3’-biindole (3)
1 H NMR (CDCl 3 , 300 MHz)
13 C NMR (CDCl 3 , 75 MHz)
155.6384 150.2233 137.9284 136.3469 131.4930 130.4071 128.3810 127.6303 123.7895 122.4777 117.2157 117.0627 114.4535
( 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 1 8 0
NH-2,2’-biindole (41)
1 H NMR (acetone-d 6 , 300 MHz)
13 C NMR (acetone-d 6 , 75 MHz)
7.5864 7.5608 7.4355 7.4089 7.1561 7.1327 7.1094 7.1061 7.0637 7.0400 7.0144 6.9461 2.9176
( 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
3,3'-(cyclohexane-1,1-diyl)bis(1H-indole) (42).
1 H NMR (CDCl 3 , 300 MHz)
138.2309 132.4004 130.0027 122.8166 121.0238 120.5573 111.8262 99.5458
( 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 1 8 0 1 9 0 2 0 0 2 1 0