Sodium hydride → 1-(Cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

7-Methoxyindole-3-carboxylic acid (3.0 g, 16.6 mmol) was added portionwise to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 1.56 g, 39 mmol) in dimethylformamide (75 ml). After 1 h, bromomethylcyclohexane (5.7 g, 32.3 mmol) was added. The mixture was heated to 60° C. with stirring for 1 h. The mixture was diluted with water (250 ml) and washed with ethyl acetate and then diethyl ether. The aqueous phase was acidified to pH 1 using 5 M hydrochloric acid and the precipitate filtered off. The crude product was recrystallised from ethyl acetate to afford 1-(cyclohexylmethyl)-7-methoxyindole-3-carboxylic acid (3.75 g) as a crystalline solid.

Provenance & Evidence