Hydrochloric Acid → 6-chloro-5-[4-(2-oxopyrrolidin-1-yl)phenyl]-1H-indole-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl 6-chloro-5-[4-(2-oxopyrrolidin-1-yl)phenyl]-1H-indole-3-carboxylate (112 mg, 0.30 mmol) in methanol (3 mL) and water (3 mL) was added sodium hydroxide (36 mg, 0.94 mmol). The reaction mixture was heated at 75° C. and stirred for 48 hours. The mixture was acidified to pH=4 using 1 N hydrochloric acid and concentrated to give a brown solid. It was purified by reverse phase HPLC to give the title compound (40 mg, 37% yield) as a pale solid. MS (ES+) 355.1 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 12.11 (br. s, 1 H), 11.95 (br. s, 1 H), 8.07 (s, 1 H), 7.95 (s, 1 H), 7.75 (d, 2 H), 7.62 (s, 1 H), 7.43 (d, 2 H), 3.89 (t, 2 H), 2.53 (m, 2 H), 2.09 (m, 2 H).

Provenance & Evidence