[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[N:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].C(OCC)(=O)C.[H][H]>C(O)C.[Pt](=O)=O>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:11]2[N:18]=[CH:17][CH:16]=[CH:15][C:12]=2[C:13]#[N:14])[CH:4]=1A solution of 2-(2-fluoro-5-nitrophenyl)nicotinonitrile (1.2 g, 4.9 mmol) and platinum(IV) oxide in ethanol (50 ml) with ethyl acetate (50 ml) was reduced under 40 psi hydrogen for 30 minutes then filtered and the solvent removed to give an orange oil. Purification by chromatography (silica gel, 1% MeOH/CH2Cl2) gave 2-(5-amino-2-fluorophenyl)-nicotinonitrile as an orange oil: 1H NMR (360 MHz, CDCl3) δ 8.88 (1H, dd, J 2, 5 Hz), 8.07 (1H, dd, J 2, 8 Hz), 7.42 (1H, dd, J 5, 8 Hz), 7.04 (1H, t, J 9 Hz), 6.85 (1H, dd, J 3, 6 Hz), 6.76-6.81 (1H, m); MS (ES+) m/z 214 [M+H]+.
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