[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([C:19]([CH3:23])([CH3:22])[C:20]#[N:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.O1CCCC1.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][C:10]([C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
2-(1-Benzyl-5-phenyl-1H-pyrazol-3-yl)-2-methylpropanenitrile (50 mg, 0.16 mmol) was dissolved in THF (1.6 mL). Borane-tetrahydrofuran (0.8 mL, 1 M solution) was added and the reaction was heated to 60° C. for 3 h. Minimal water was added to quench the reaction. Ethyl acetate was added followed by sodium sulfate and the solids were removed by filtration. The filtrate was concentrated under reduced pressure to yield 2-(1-benzyl-5-phenyl-1H-pyrazol-3-yl)-2-methylpropan-1-amine (50 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C20H23N3: 305.19. found: 306.2 (M+H)+.
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