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Sodium borohydride → 2-(4-(Hydroxymethyl)-1H-indol-1-yl)benzonitrile

HRID 1055402
Notes
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Reaction equation

HRID 1055402 reaction equation
[BH4-].[Na+].[CH:3]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17])=[O:4]>CCO.C(Cl)Cl>[OH:4][CH2:3][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][N:9]2[C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[C:16]#[N:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 900374192-(4-formyl-1H-indol-1-yl)benzonitrile

Product 1

HCID 189504042-(4-(Hydroxymethyl)-1H-indol-1-yl)benzonitrileYield 99.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

NaBH4 (50 mg, 1.35 mmol Eq: 0.4) was added to a solution of 2-(4-formyl-1H-indol-1-yl)benzonitrile (810 mg, 3.29 mmol, Eq: 1.00) in EtOH (30 mL) and DCM (15 mL) at 0° C. and the mixture warmed to RT. After 3 h., the mixture was concentrated to remove the DCM. The resulting mixture was diluted with sat. NH4Cl, extracted with DCM and the combined extracts concentrated. The residue was purified by silica gel chromatography to afford the title compound (810 mg, 99%) as a white solid.

Workup

  1. concentrationthe mixture was concentrated
  2. customto remove the DCM
  3. additionThe resulting mixture was diluted with sat. NH4Cl
  4. extractionextracted with DCM
  5. concentrationthe combined extracts concentrated
  6. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-74518f6644234fe796b3a4c9b7f9c9fb
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394263B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes