Sodium hydride → 2-(2-chloro-3-formyl-1H-indol-1-yl)benzonitrile

HRID 1055399Notes

Reaction equation

HRID 1055399 reaction equation
[H-].[Na+].[Cl:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.F[C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>CN1CCCC1=O.[NH4+].[Cl-]>[Cl:3][C:4]1[N:5]([C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[C:18]#[N:19])[C:6]2[C:11]([C:12]=1[CH:13]=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 678552-FluorobenzonitrileHCID 3147912-chloro-1H-indole-3-carbaldehyde

Product 1

HCID 900367652-(2-chloro-3-formyl-1H-indol-1-yl)benzonitrileYield 8%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
150 °C

Procedure

NaH (60% in mineral oil, 223 mg, 5.57 mmol, Eq: 1.00) was added to a solution of 2-chloro-1H-indole-3-carbaldehyde (1 g, 5.57 mmol, Eq: 1.00) in 1-methyl-2-pyrrolidinone (NMP, 5 mL) in a microwave vial. After 10 min., 2-fluorobenzonitrile (3.37 g, 3.02 mL, 27.8 mmol, Eq: 5) was added. The reaction was sealed and heated at 150° C. After 16 h. the mixture was diluted with sat. NH4Cl solution, extracted with EtOAc and the combined extracts concentrated to give a residue that was purified by silica gel chromatography to afford 2-(2-chloro-3-formyl-1H-indol-1-yl)benzonitrile (120 mg, 8%) as a light brown solid.

Workup

  1. customThe reaction was sealed
  2. extractionextracted with EtOAc
  3. concentrationthe combined extracts concentrated
  4. customto give a residue that
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-d09007d136d14fe09c5ac77c2b6e43c5
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…