3-Fluoro-2-(2-fluoro-5-nitrophenyl)pyridine → 4-Fluoro-3-(3-fluoropyridin-2-yl)phenylamine

Reaction equation

[F:1][C:2]1[C:3]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[F:17])=[N:4][CH:5]=[CH:6][CH:7]=1>ClCCl.C(O)C.[Pt]=O>[F:17][C:9]1[CH:10]=[CH:11][C:12]([NH2:14])=[CH:13][C:8]=1[C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

Procedure

3-Fluoro-2-(2-fluoro-5-nitrophenyl)pyridine (1.0 g) was dissolved in dichloromethane (25 ml) and diluted with ethanol (50 ml). Platinum oxide (0.1 g) was added, and the mixture shaken on a Parr hydrogenation apparatus under an atmosphere of hydrogen at 45 psi for 4 h. The reaction was filtered and the filtrate evaporated, to afford 4-fluoro-3-(3-fluoropyridin-2-yl)phenylamine, which was used without further purification: 19F NMR (400 MHz, CDCl3) δ 128.48 (1F, d, J 36 Hz), 122.66 (1F, d, J 36 Hz).