HCID 69760821, compound → HCID 60026668, compound

Participants

Reaction Steps

A mixture of the above 2-(1-benzenesulfonyl-5-pyridin-2-yl-1H-indol-2-ylmethyl)-4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-ol (30.1 mg, 0.046 mmol, theoretical maximum from above) in 5 mL of methanol and 5 mL of 10% aqueous sodium hydroxide solution was warmed at reflux. After 4 hours, the mixture was diluted with 7 mL of brine and extracted with three 5 mL portions of ethyl acetate. The combined organic layers were washed with three 5 mL portions of saturated aqueous sodium bicarbonate solution, 5 mL of brine, two 5 mL portions of saturated aqueous ammonium chloride solution, 5 mL of brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel preparative TLC using ethyl acetate-hexanes (1:1). The material from the preparative TLC plate when concentrated in vacuo from diethyl ether-hexanes afforded 10 mg (42% yield) of the title compound.

Provenance & Evidence