Sodium Hydroxide → HCID 22497255, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2,2-trifluoro-1-(1-isopropyl-6-methylsulfanyl-1H-indol-3-yl)-ethanone (200 mg, 0.77 mmol) in tetrahydrofuran (1 mL) at 25° C. was treated with a 20% aqueous sodium hydroxide solution (2 mL). The mixture was heated at 100° C. for 24 h. At this time, the reaction was cooled to 25° C. and was partitioned between water (40 mL) and ethyl acetate (40 mL). The solution was treated with a 1N aqueous hydrochloric acid solution. The layers were then shaken and separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 2/1 hexanes/ethyl acetate) afforded 1-isopropyl-6-methylsulfanyl-1H-indole-3-carboxylic acid (126 mg, 77%) as a white solid: mp 132-133° C.; EI-HRMS m/e calcd for C13H15NO2S (M+) 249.0823, found 249.0819.

Provenance & Evidence