Benzyl Chloride → Methyl 1-(phenylmethyl)-1H-indole-6-carboxylate

HRID 878936Notes

Reaction equation

HRID 878936 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:20]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 3940732Methyl 1-(phenylmethyl)-1H-indole-6-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl indole-6-carboxylate (1.0 g) in N,N-dimethylformamide (10 mL), potassium carbonate (1.2 g) and benzyl chloride (1.4 g) were added at room temperature, and then the reaction mixture was stirred at 60° C. for 3 hours. After cooling to room temperature, the reaction mixture was quenched with water, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (681 mg) as a colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was quenched with water
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cf92043638354b589b0a0d551f316a57
Source dataset
uspto-grants-2015_03
Patent number
US08987473B2

Reaction notes

Loading…