Ethanol → 5-Bromo-3-isopropyl-1H-indole-7-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-bromo-3-(1-methylethyl)-1H-indole-7-carbonitrile (1.66 g, 6.31 mmol) in EtOH (45 mL) and water (15 mL) was added 6 N NaOH (10 mL, 60.0 mmol). The reaction was heated at reflux (100° C. oil bath) under N2 for 72 h. LCMS showed that the reaction was complete after 24 h. The reaction was cooled to RT, evaporated to near dryness, diluted with water (˜100 mL), and acidified with 6 N HCl (10 mL). The suspension was triturated, filtered, washed with water and dried under vacuum to give the product 5-bromo-3-(1-methylethyl)-1H-indole-7-carboxylic acid (2.29 g, 8.12 mmol, 129% yield) as an off-white solid. MS (ES)+ m/e 282.4 [M+H]+.

Provenance & Evidence