Dimethylformamide → 6-Chloro-1,2-dimethyl-1H-indole-3-carboxylic acid methyl ester

HRID 2261843Notes

Reaction equation

HRID 2261843 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH3:15])=[O:4].[C:16](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[N:7]([CH3:16])[C:6]=1[CH3:15])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57443356methyl 6-chloro-2-methyl-1H-indole-3-carboxylate

Product 1

HCID 574433576-Chloro-1,2-dimethyl-1H-indole-3-carboxylic acid methyl esterYield 55.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-chloro-2-methyl-1H-indole-3-carboxylic acid methyl ester (2.76 g, 12.3 mmol), potassium carbonate (6.80 g, 49.2 mmol), iodomethane (1.07 mL, 17.2 mmol) and DMF (36 mL) is stirred overnight at room temperature. The mixture is diluted with ethyl acetate, washed twice with water, washed with brine and dried (MgSO4) and concentrated. The residue is triturated in 25 mL of 1:3 ethyl acetate-heptane and filtered to provide 1.63 g (55%) of pure title product. Additional material can be obtained through further trituration of the mother liquor. ES/MS m/e 238.0 (M+1).

Workup

  1. washwashed twice with water
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is triturated in 25 mL of 1:3 ethyl acetate-heptane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-a725026dd39e47ea924ac6d0a3c206d1
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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