Potassium Hydroxide → HCID 10179618, compound

Participants

Reaction Steps

To a solution of 5-[3-(Cyclobutyl-methyl-carbamoyl)-4-hydroxy-phenoxy]-4,6-dimethyl-1H-indole-2-carboxylic acid ethyl ester (102 mg, 0.23 mmol) in methanol (2 mL) at room temperature was added 3N potassium hydroxide (0.44 mL) and the mixture was stirred at room temperature for 7 hours. The reaction mixture was diluted with water (10 mL) and washed with EtOAc/Et2O (1/1, 3 times 5 mL). The aqueous solution was acidified with hydrochloric acid and then extracted with ethyl acetate (3 times 5 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to afford the title compound (81 mg) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ11.08 (s, 1H), 7.15-7.14 (d, 2H), 6.76 (s+m, 2H), 6.33 (br s, 1H), 4.25-4.16 (m, 1H), 2.90 (s, 3H), 2.25 (s, 3H), 2.22-2.19 (m, 2H), 2.15 (s, 3H), 1.95-1.85 (m, 2H), 1.60-1.48 (m, 2H). MS (APCI+) Calc: 408.2, Found: 409.2 (M+1).

Provenance & Evidence