L-(+)-Cysteine → (2-(1H-indol-2-yl)thiazol-4-yl)(1H-indol-5-yl)methanone

Reaction equation

C1(C2SC=[C:10]([C:12]([C:14]3[CH:19]=[C:18](OC)[C:17](OC)=[C:16](OC)[CH:15]=3)=O)[N:11]=2)C=CC=CC=1.[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[C:35]1[S:36][CH2:37][CH:38]([C:40]([OH:42])=O)[N:39]=1.N[C@H](C(O)=O)CS>>[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[C:27]1[C:35]1[S:36][CH:37]=[C:38]([C:40]([C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[NH:11][CH:10]=[CH:12]3)=[O:42])[N:39]=1

Participants

Reactant 3

HCID 5862L-(+)-Cysteine

HCID 252274304-(3,4,5-Trimethoxybenzoyl)-2-phenylthiazole

HCID 575168342-(1H-indol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

Product 1

HCID 136047813(2-(1H-indol-2-yl)thiazol-4-yl)(1H-indol-5-yl)methanone

Procedure

(2-(1H-indol-2-yl)thiazol-4-yl)(1H-indol-5-yl)methanone (21) was prepared using the similar method as used of compound 1h from 2-(1H-indol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid and cysteine. 1H NMR (500 MHz, CDCl3) δ 9.60 (s, 1H), 9.26 (s, 1H), 8.31 (s, 1H), 8.03 (s, 1H), 7.83 (dd, 1H), 7.69 (d, 1H), 7.53-7.49 (m, 2H), 7.41 (t, 1H), 7.33 (t, 1H), 7.21-7.18 (m, 2H), 7.13 (s, 1H). MS (ESI) m/z 366.1 (M+Na)+, 341.9 (M−H)−.