Sodium hydride → 2-(4-formyl-1H-indol-1-yl)benzonitrile

HRID 1055401Notes

Reaction equation

HRID 1055401 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:12]=[O:13])[C:6]=2[CH:5]=[CH:4]1.F[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18]>CN(C=O)C.[NH4+].[Cl-]>[CH:12]([C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][N:3]2[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18])=[O:13]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 678552-FluorobenzonitrileHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 900374192-(4-formyl-1H-indol-1-yl)benzonitrileYield 70.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

NaH (60% in mineral oil, 303 mg, 7.58 mmol, Eq: 1.1) was added to a solution of 1H-indole-4-carbaldehyde (1 g, 6.89 mmol, Eq: 1.00) in DMF (12 mL) at 0° C. After 10 min., the mixture was warmed to RT and treated with sonication for 2 min. 2-Fluorobenzonitrile (918 mg, 822 μl, 7.58 mmol, Eq: 1.1) was added and the mixture was treated with sonication for 3 min. After 3 h the mixture was diluted with sat. NH4Cl, extracted with EtOAc, the combined extracts washed with H2O and concentrated. The residue was tritrurated with Hexane/Et2O to give 2-(4-formyl-1H-indol-1-yl)benzonitrile (1.2 g, 70.7%) as a grey solid.

Workup

  1. additiontreated with sonication for 2 min
  2. additionthe mixture was treated with sonication for 3 min
  3. extractionextracted with EtOAc
  4. washthe combined extracts washed with H2O
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-474a944eace34c10975875401f575ba6
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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