Methyl iodide → HCID 59497666, compound

Participants

Reaction Steps

A solution of the 5-bromo-indole-7-carboxylic acid methyl ester (300 mg, 1.18 mmol) in DMF (15 mL) was cooled to 0° C. under nitrogen and treated with sodium hydride (60% in mineral oil) (56.6 gm, 1.4 mmol). After stirring for 15 minutes the iodomethane (0.08 mL, 1.3 mmol) was introduced and the cooling bath was removed (reaction became light purple). After 30 minutes the reaction was quenched with water (5 ml) and then concentrated to reduce the volume of DMF. The reaction was poured into water (1.6 L) and EtOAc (200 ml). The layers were separated and the aqueous phase was extracted with EtOAc (3×200 ml). The combined organics were washed with water (3×) and then dried (MgSO4). The solution was filtered and the filterate was concentrated. The residue was purfied by CombiFlash with 10% EtOAc in Hexane as the eluent to afford the desirable product 5-Bromo-1-methyl-1H-indole-7-carboxylic acid methyl ester (290 mg, 92%) as a white solid.

Provenance & Evidence