Sodium Carbonate → 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxothiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide

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Reaction Steps

5.0 g (8.3 mmol) 2-(3,5-Bis-trifluoromethyl-phenyl)-N-methyl-N-[4-(4-fluoro-2-methyl-phenyl)-6-thiomorpholin-4-yl-pyridin-3-yl]-isobutyramide was suspended in 50 ml methanol and treated at room temperature with 6.4 g (10.4 mmol) oxone™. The suspension was stirred for 16 hours at room temperature, cooled to 0° C. and 3.4 ml (16.7 mmol) sodium hydrogen sulfite solution was added dropwise. The stirring was pursued for 30 minutes at room temperature and the pH adjusted to ca. 8.5 with saturated aqueous sodium carbonate. The methanol was evaporated under reduced pressure and the residue was extracted with dichloromethane. The organic phase was washed with half-saturated aqueous sodium chloride. The solvent was exchanged under reduced pressure in a rotary evaporator with 60 ml isopropanol and the volume reduced to ca. 40 ml. The solution was cooled to room temperature under stirring within 2 hours and stirred further for 1 hour. The precipitate formed was filtered off, washed with 5 ml isopropanol and dried under high vacuum to yield 4.4 g (83.5%) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-(1,1-dioxothiomorpholin-4-yl)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide as a white powder of m.p.=135–138° C.

Provenance & Evidence