5-Fluoroindole-2-carboxylic acid → 5-Fluoro-1H-indole-2-carboxylic acid [(1S)-(4-fluoro-benzyl)-2-morpholin-4-yl-2-oxo-ethyl]-amide
Reaction equation
Cl.[NH2:2][C@@H:3]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)[C:4]([N:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1)=[O:5].[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([C:30](O)=[O:31])=[CH:24]2>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C@H:3]([NH:2][C:30]([C:25]2[NH:26][C:27]3[C:23]([CH:24]=2)=[CH:22][C:21]([F:20])=[CH:29][CH:28]=3)=[O:31])[C:4]([N:6]2[CH2:11][CH2:10][O:9][CH2:8][CH2:7]2)=[O:5])=[CH:14][CH:15]=1Participants
3
Procedure
(S)-2-Amino-3-(4-fluoro-phenyl)-1-morpholin-4-yl-propan-1-one hydrochloride (0.48 mmol) and 5-fluoro-1H-indole-2-carboxylic acid (0.48 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 48 hour reaction time, washed with acid first then base) and the product purified by chromatography on silica gel eluted with 20, 30, 40, 50 and 75% ethyl acetate in hexanes. Yield 189 mg, 95%; HPLC (60/40) 4.76 minutes (97%); PBMS 414 (MH+, 100%);