Dimethylformamide → Methyl 6-bromo-1-methyl-1H-indole-3-carboxylate

HRID 424785Notes

Reaction equation

HRID 424785 reaction equation
COC(C1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Br:14])[CH:12]=2)NC=1)=O.[C:15](=[O:18])([O-])[O-:16].[K+].[K+].I[CH3:22].[CH3:23][N:24]([CH:26]=O)[CH3:25]>ClCCl>[CH3:22][O:16][C:15]([C:13]1[C:8]2[C:23](=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[N:24]([CH3:25])[CH:26]=1)=[O:18]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 285091Methyl 5-bromo-1H-indole-3-carboxylate

Product 1

HCID 57443279Methyl 6-bromo-1-methyl-1H-indole-3-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-bromo-1H-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) in DMF is added iodomethane (30 μL, 0.47 mmol). The reaction mixture is stirred for 1.5 hours. Additional iodomethane (10 μL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give 105 mg (99%) of the title compound. ES/MS m/e 270.0 (M+2).

Workup

  1. stirringthe reaction is stirred for 30 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated under high vacuum
  4. additiondiluted with ethyl acetate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3d3510a86f1f4abe8d158c93f33bd81e
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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