Hydrochloric Acid → HCID 178524786, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloro-5-[4-(trans-3-hydroxycyclobutyl)phenyl]-1H-indole-3-carboxylate (290 mg, 0.82 mmol) in methanol/water (20 mL, v/v=1/1) was added sodium hydroxide (326 mg, 8.17 mmol). The mixture was stirred at 90° C. for 5 hours. The mixture was then acidified with 1 M HCl to pH˜5. The resulting suspension was extracted with dichloromethane. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by reverse phase HPLC to give the title compound (150 mg, 54%) as a white solid. MS (AP+) 342.0 (M+H)+: 1H NMR (500 MHz, CD3OD) δ 8.03 (s, 1 H), 8.02 (s, 1 H), 7.59 (s, 1 H), 7.41 (d, 2 H), 7.34 (d, 2 H), 4.53-4.50 (m, 1 H), 3.67-3.65 (m, 1 H), 2.55-2.43 (m, 4 H).

Provenance & Evidence