(1-Bromoethyl)benzene → HCID 89741698, compound

HRID 1527117Notes

Reaction equation

HRID 1527117 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-e66b2a85140c4c8b93cd7f0ba3b061d2
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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