Tetrabutylammonium Fluoride → HCID 60026375, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the above 2-(1-benzenesulfonyl-5-pyridin-3-yl-1H-indol-2-ylmethyl)-1,1,1-trifluoro-4-(5-fluoro-2,3-dihydrobenzofuran-7-yl)-4-methylpentan-2-ol (71 mg, 0.11 mmol) in 5 mL of THF was added a I M solution of tetrabutylammonium fluoride (0.5 mL, 0.5 mmol) in THF and the mixture was warmed at 80° C. After 18 hours, the mixture was concentrated in vacuo and diluted with 1 N aqueous sodium hydroxide solution and extracted with three 5 mL portions of ethyl acetate. The combined organic layers were washed with two 5 mL portions of 1 N aqueous sodium hydroxide solution, 5 mL of brine, three 5 mL portions of saturated aqueous ammonium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified on silica gel eluting with methanol-dichloromethane (0:100, then 0.5:99.5, then 1:99) to afford 46 mg (83% yield) of the title compound.

Provenance & Evidence