[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:19](=O)[CH3:20])=[CH:10][C:11]([CH3:18])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH:19]([NH2:28])[CH3:20])=[CH:10][C:11]([CH3:18])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1A mixture of 1-[8-(3-fluorophenyl)-5-methylquinolin-7-yl]ethanone (50 mg, 0.2 mmol) and ammonium acetate (138 mg, 1.79 mmol) in methanol (1.0 mL) and acetonitrile (1.0 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (22.5 mg, 0.358 mmol). The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate, extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step. LCMS calculated for C18H18FN2 (M+H)+: m/z=281.1; Found: 281.1.
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