Potassium Carbonate → Methyl 2-(5-chloro-2-methyl-1H-indol-1-yl)acetate

HRID 1944444Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]([CH3:15])=[CH:5]2.[C:16](=O)([O-])[O-].[K+].[K+].BrCC(OC)=O>CN(C)C=O>[CH3:16][O:13][C:12](=[O:14])[CH2:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[CH3:15]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (5-chloro-2-methylindol-1-yl)acetic acid (25 g), potassium carbonate (100 g) and N,N-dimethylformamide (220 mL) was treated dropwise with methyl bromoacetate (37 g), and the resulting mixture was stirred at 60° C. for 2 days. The mixture was cooled to room temperature and partitioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic solution was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and pentane (1:10 to 1:0 by volume) to afford the title compound as a white solid (27 g).

Workup

temperatureThe mixture was cooled to room temperature
custompartitioned between water and ethyl acetate
extractionThe aqueous layer was extracted with ethyl acetate
washthe combined organic solution was washed with saturated aqueous sodium chloride solution
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel
washeluting with a mixture of dichloromethane and pentane (1:10 to 1:0 by volume)

Sources & evidence

ORD record: ord-c032083b613143e79790eac64e61c3d4
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394836B2

Reaction notes

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