Sodium borohydride → 1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-ol
Reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[N:13]=[CH:12][C:11]([C:14](=[O:18])[CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=2)[CH:7]=1.[BH4-].[Na+]>CO>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[N:5][N:6]([C:8]2[N:13]=[CH:12][C:11]([CH:14]([OH:18])[CH2:15][CH2:16][CH3:17])=[CH:10][CH:9]=2)[CH:7]=1Participants
4
Procedure
1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-one (140 mg, 0.49 mmol) was dissolved in 5 mL methanol. Sodium borohydride (18.7 mg, 0.494 mmol) was added. The reaction mixture was concentrated and the residue partitioned between water and ethyl acetate. The organic layer was concentrated to give 1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-ol (140 mg). 1H NMR (400 MHz, CDCl3) δ 8.84 (s, 1H), 8.34-8.40 (m, 1H), 7.96 (d, J=8.4 Hz, 1H), 7.82-7.90 (m, 2H), 4.75-4.82 (m, 1H), 1.64-1.89 (m, 2H), 1.27-1.53 (m, 2H), 0.94 (t, J=7.4 Hz, 3H).