(Trifluoromethyl)trimethylsilane → N-(1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl)-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-((5-bromopyridin-3-yl)methylene)-2-methylpropane-2-sulfinamide (10.75 mmol) and tetrabutylammonium difluorotriphenylsilicate(IV) (6.38 g, 11.83 mmol) in THF (53.8 ml) was cooled to −78° C. Then (trifluoromethyl)trimethylsilane 2M solution in THF (6.45 ml, 12.90 mmol) was added dropwise, and the mixture stirred at −78° C. for 2 h. Brine was added and the precipitate removed and washed with AcOEt. The filtrates were dried over MgSO4, filtered and concentrated. The residue was purified via Biotage (0-15% MeOH/CH2Cl2; SNAP50 column) giving the title compound (2.96 g, 77%) as a light yellow solid. LC-MS (M+1) 361.0.

Provenance & Evidence