Morpholine → (4S,5R)-5-[3,5-Bis(trifluoromethyl)phenyl]-3-{[3-bromo-6-(morpholin-4-yl)pyridin-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

Triethylamine (3.23 mL, 23.18 mmol), morpholine (1.683 mL, 19.32 mmol), (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 24, 2 g, 3.86 mmol) and 1,4-dioxane (10.0 mL) were mixed in a 20 mL microwave vial, capped and heated at 140° C. for 6 hours in microwave with monitoring by TLC and LCMS. Once the reaction was determined to be complete, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous NaHCO3, water and brine. The organic phase was dried with Na2SO4, filtered and the filtrate concentrated. The crude was purified by silica gel chromatography in 30% ethyl acetate/hexanes to give the titled compound (1.8 g, 3.17 mmol, 82% yield) as white solid. LCMS (M+H)+: 569.9. 1H NMR (CDCl3, 500 MHz): δ 7.93 (s, 1H), 7.80 (s, 2H), 7.63 (dd, 1H), 6.52 (d, 1H), 5.75 (d, 1H), 4.91 (d, 1H), 4.32 (d, 1H), 4.28 (t, 1H), 3.87-3.84 (t, 4H), 3.57-3.48 (m, 4H), 0.83 (d, 3H).

Provenance & Evidence