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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 424785Generated: October 30, 2026

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

https://huagongshe.com/reaction/424785

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantMethyl iodideHCID 6328—
ReactantPotassium CarbonateHCID 11430—
ReactantMethyl 5-bromo-1H-indole-3-carboxylateHCID 285091—
SolventDichloromethaneHCID 6344—
ProductMethyl 6-bromo-1-methyl-1H-indole-3-carboxylateHCID 5744327999%

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08106077B2
Source datasetuspto-grants-2012_01
ORD IDord-3d3510a86f1f4abe8d158c93f33bd81e
Source noteuspto-grants-2012_01