Sodium borohydride → 1-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-ol

HRID 537504Notes

Reaction equation

HRID 537504 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]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 681567451-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-one

Product 1

HCID 681577581-(6-(4-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-3-yl)butan-1-olYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between water and ethyl acetate
  3. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-5a1797d0c95b43d1895855a1eb017f2b
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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