(5-Fluoro-2-nitrophenyl)pyridin-3-ylamine → 4-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine
反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-])=O)=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=1>CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[C:5]([NH2:15])=[CH:4][CH:3]=1参加物
3
実験手順
A mixture of (5-fluoro-2-nitrophenyl)pyridin-3-ylamine (1.28 g, 5.49 mmol) in EtOAc (60 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (107 mg) and was stirred at RT under a hydrogen atmosphere for 2 h. The resulting suspension was diluted with IMS (10 mL) and stirred under a hydrogen atmosphere for 56 h. The reaction mixture was filtered through a phase separator and the filtrate concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% MeOH in DCM) to afford the title compound as a brown solid (1.03 g, 92%). 1H NMR (CDCl3, 400 MHz): δ 8.24 (1H, d, J=2.67 Hz), 8.14 (1H, d, J=4.50 Hz), 7.20-7.05 (2H, m), 6.86 (1H, dd, J=9.62, 2.63 Hz), 6.79-6.65 (2H, m), 5.42 (1H, s), 3.50 (2H, s)