Sodium borohydride → HCID 44479602, compound

HRID 2067970Notes

Reaction equation

HRID 2067970 reaction equation
[O:1]=[CH:2][CH2:3][C@H:4]([NH:15][C:16]([C:18]1[CH:19]=[N:20][N:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:22]=1[CH3:23])=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1.[BH4-].[Na+]>CO>[OH:1][CH2:2][CH2:3][C@H:4]([NH:15][C:16]([C:18]1[CH:19]=[N:20][N:21]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:22]=1[CH3:23])=[O:17])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58443395HCID 58443395, compound

Product 1

HCID 44479602HCID 44479602, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [(S)-3-oxo-1-(3-trifluoromethyl-phenyl)-propyl]-amide (80 mg, 0.18 mmol) in methanol (3 mL) is added sodium borohydride (50 mg, 1.3 mmol). After 16 hours, the crude reaction mixture is purified directly by flash chromatography on silica gel (eluted with 4 to 10% MeOH/CH2Cl2) to afford 1-(4-chloro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid [(S)-3-hydroxy-1-(3-trifluoromethyl-phenyl)-propyl]-amide as a white solid (36 mg, 45%).

Workup

  1. customthe crude reaction mixture
  2. customis purified directly by flash chromatography on silica gel (eluted with 4 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-b6fb6062c0784fa8bf21559b3d2d0570
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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