[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[C:18](=O)[CH3:19])[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:27].[Na+]>CO.C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:17])=[C:9]2[CH:18]([NH2:27])[CH3:19])[CH:5]=[CH:6][CH:7]=1A mixture of 1-[1-(3-fluorophenyl)-3-methyl-1H-indol-2-yl]ethanone (0.165 g, 0.617 mmol) and ammonium acetate (0.476 g, 6.17 mmol) in methanol (2.0 mL) and acetonitrile (2.0 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, sodium cyanoborohydride (0.12 g, 1.9 mmol) was added to the resultant mixture. The reaction was heated at 65° C. over the weekend. The reaction was cooled to room temperature and quenched with saturated NaHCO3 solution and then extracted with dichloromethane, dried over MgSO4 and concentrated to give the crude amine (0.16 g), which was used directly in next step. LCMS calculated for C17H18FN2(M+H)+: m/z=269.1. Found: 252.1.
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