Water → HCID 86692444, compound

HRID 1748480Notes

Reaction equation

HRID 1748480 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[NH:10][CH:9]=1)=[O:7])[CH3:4].[CH3:18]I.O>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Br:17])[CH:15]=2)[N:10]([CH3:18])[CH:9]=1)=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 44155267Ethyl 5-bromo-1H-indole-3-carboxylate

Product 1

HCID 86692444HCID 86692444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (537 mg) was added to a solution of 5-bromo-1H-indole-3-carboxylic acid ethyl ester (3.00 g) in N,N-dimethylformamide (22 ml) at room temperature, and stirred at the same temperature for 0.5 hour. Methyl iodide (2.1 ml) was added and the mixture was stirred at the same temperature for two hours. After completion of the reaction, water was added and the precipitated solid was collected by filtration. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 5-bromo-1-methyl-1H-indole-3-carboxylic acid ethyl ester (3.10 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at the same temperature for two hours
  2. additionwas added
  3. filtrationthe precipitated solid was collected by filtration
  4. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-39dd9a37da764d529fe3f934ee30c8ca
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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