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

HRID 1689783Notes

Reaction equation

HRID 1689783 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=[O:4].[C:15](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[N:7]([CH3:15])[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 11499811Methyl 6-Bromo-1H-Indole-3-Carboxylate

Product 1

HCID 57443279Methyl 6-bromo-1-methyl-1H-indole-3-carboxylateYield 99.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-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 h. 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 the title compound (105 mg, 99%). 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-7dfb928d468248a3b09d3a19c232cb54
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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