Sodium borohydride → HCID 178527316, compound

HRID 2274794Notes

Reaction equation

HRID 2274794 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([CH:25]4[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([C@H:25]4[CH2:26][CH2:27][C@H:28]([OH:31])[CH2:29][CH2:30]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118060440HCID 118060440, compound2×

Product 1

HCID 178527316HCID 178527316, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)cyclohexanone (Intermediate 48; 197 mg; 0.45 mmol) in MeOH (15 mL) was added NaBH4 (34 mg; 0.90 mmol). The reaction mixture was stirred overnight, concentrated, and purified by preparative TLC (DCM/MeOH=20/1) to afford 32 mg (16%) of the title compound as a white solid.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative TLC (DCM/MeOH=20/1)

Sources & evidence

ORD record
ord-1933f221f4134adca12467400c042cd8
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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