(Trifluoromethyl)trimethylsilane → 6-bromo-2-(4-methanesulfonylbenzyl)-4-phenyl-3-(2,2,2-trifluoro-1-hydroxyethyl)-2H-isoquinolin-1-one

Participants

Reaction Steps

To a solution (5 ml) of 6-bromo-2-(4-methanesulfonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carbaldehyde (500 mg) and (trifluoromethyl)trimethylsilane (170 mg) in THF was added a solution of tetra-N-butylammonium fluoride (1M, 0.03 ml) in THF at room temperature, and the mixture was stirred for 30 min. Then a solution (1M, 2 ml) of tetra-N-butylammonium fluoride in THF was added, and the mixture was stirred for 30 min. The reaction mixture was concentrated under reduced pressure and the residue was diluted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (THF) and basic silica gel column chromatography (THF) and the crystals were washed with a mixture of ethyl acetate and diisopropyl ether, and recrystallized (MeOH-hexane) to give the title compound (290 mg).

Provenance & Evidence