(1-Bromoethyl)benzene → HCID 89741698, compound

HRID 2206630Notes

Reaction equation

HRID 2206630 reaction equation
[Br:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].Br[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19]>CN(C)C=O.O>[Br:1][C:2]1[N:3]([CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

6

Reactant 3

HCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 89739680HCID 89739680, compound

Product 1

HCID 89741698HCID 89741698, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-bromo-1H-indole-3-carboxylate (1.0 g, 4.0 mmol) in dimethylformamide was added sodium hydride (0.32 g, 8.0 mmol, 60% in oil) under ice bath. The resulting mixture was stirred at room temperature for 0.5 hour. Then (1-bromoethyl)benzene (1.1 g, 6.0 mmol) was added in portion slowly. Then the mixture was stirred at room temperature for 1 hour. After the reaction, it was diluted with water (100 mL), and the product was extracted with ethyl acetate (100 mL), dried over anhydrous sodium sulfate, concentrated and purified by column Chromatography (silica gel: ethyl acetate:petroleum ether=1:8) to give the pure product methyl 2-bromo-1-(1-phenylethyl)-1H-indole-3-carboxylate (1.1 g, 75%) as a yellow oil.

Workup

  1. stirringThen the mixture was stirred at room temperature for 1 hour
  2. customAfter the reaction, it
  3. extractionthe product was extracted with ethyl acetate (100 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified by column Chromatography (silica gel: ethyl acetate:petroleum ether=1:8)

Sources & evidence

ORD record
ord-e8c812bfedbc46a79c7d855939797589
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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