HCID 12150668, compound → HCID 10111204, compound

Participants

Reaction Steps

To a solution of 4,6-dichloro-5-(4-hydroxy-3-isopropyl-phenoxy)-1-methyl-1H-indole-2-carboxylic acid methyl ester (32 mg, 0.078 mmol) in 50% aqueous MeOH (4 mL) was added potassium hydroxide (3N, 154 μL). The resulting solution was stirred for 19 hours at room temperature, diluted with potassium hydroxide (0.1N, 16 mL) and the solution was washed with EtOAc (3 times 10 mL). The aqueous solution was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate (3 times 15 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated to afford the title compound (23 mg). 1H NMR (400 MHz, CD3OD) δ7.64 (s, 1H), 7.24 (s, 1H), 6.63 (d, 1H), 6.57 (d, 1H), 6.29-6.26 (dd, 1H), 4.03 (s, 3H), 3.22-3.15 (m, 1H), 1.11 (d, 6H). MS (APCI−) Calc: 393.0, Found: 392.2 (M−1).

Provenance & Evidence