Sodium borohydride → 2-(2-Chloro-3-(hydroxymethyl)-1H-indol-1-yl)benzonitrile

HRID 1055400Notes

Reaction equation

HRID 1055400 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[N:5]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]#[N:18])[C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2>C(Cl)Cl.CO.[NH4+].[Cl-]>[Cl:3][C:4]1[N:5]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]#[N:18])[C:6]2[C:11]([C:12]=1[CH2:13][OH:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 900367652-(2-chloro-3-formyl-1H-indol-1-yl)benzonitrile

Product 1

HCID 900376432-(2-Chloro-3-(hydroxymethyl)-1H-indol-1-yl)benzonitrileYield 100.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

NaBH4 (6 mg, 159 μmol, Eq: 0.387) was added to a solution of 2-(2-chloro-3-formyl-1H-indol-1-yl)benzonitrile (115 mg, 410 μmol, Eq: 1.00) in DCM (3 mL) and MeOH (3.00 mL) at 0° C. and the mixture brought to RT. After 2 h 15 min. the mixture was diluted with sat. NH4Cl and extracted with DCM and the extracts concentrated to afford the title compound (116 mg, 100%) which was used without purification.

Workup

  1. custombrought to RT
  2. extractionextracted with DCM
  3. concentrationthe extracts concentrated

Sources & evidence

ORD record
ord-0cd42b398bd1422f9ea10dc4022d9149
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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