Sodium Hydroxide → 6-Fluoro-1-(propan-2-yl)-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2,2-trifluoro-1-(6-fluoro-1-isopropyl-1H-indol-3-yl)-ethanone (1.65 g, 6.04 mmol) in a 20% aqueous sodium hydroxide solution (25 mL) was heated at 110° C. for 18 h. At this time, the reaction was cooled to 25° C., partitioned between water (50 mL) and ethyl acetate (50 mL), and treated with a 1N aqueous hydrochloric acid solution (50 mL). The organic layer was washed with a saturated aqueous sodium chloride solution (1×100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 6-fluoro-1-isopropyl-1H-indole-3-carboxylic acid (1.29 g, 96%) as a yellow solid: mp 177-180° C.; EI-HRMS m/e calcd for C12H12FNO2 (M+) 221.0852, found 221.0850.

Provenance & Evidence