4-Methyl-2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-nitro-indol-1-yl)-amide → 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amide
반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH:13][C:14]([C:16]1[C:17]([CH3:29])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[N:20][CH:21]=1)=[O:15])[CH:8]=[CH:7]2)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([NH:13][C:14]([C:16]1[C:17]([CH3:29])=[N:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)=[N:20][CH:21]=1)=[O:15])[CH:8]=[CH:7]2참가 물질
4
실험 절차
A solution of 4-methyl-2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid (5-nitro-indol-1-yl)-amide (1.64 mmol) in MeOH (45 mL) and 10% Pd/C (0.16 mmol) is hydrogenated in a 500 mL Parr bottle under 50 psi at rt overnight. Pd/C is filtered off. The filtrate is concentrated to afford 2-(3-fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-amino-indol-1-yl)-amide (545 mg, 92%) as a solid. MS: 362 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.84(s, H), 6.37(d, H), 6.81(dd, H), 7.01(d, H), 7.16-7.36(m, 3H), 7.55(m, H), 8.23(d, H), 8.36(d, H), 9.50(s, H).