Tetrahydrofuran → methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-chloropyridin-3-yl]-4-methoxyphenyl}acetate

Participants

Reaction Steps

A flask was charged with (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[(3-bromo-6-chloropyridin-2-yl)methyl]-4-methyl-1,3-oxazolidin-2-one (265 mg, 0.511 mmol), methyl [4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate (156.6 mg, 0.511 mmol), 1M K2CO3 (4 mL, 4 mmol), and THF (4 mL). The reaction was degassed with N2 and then 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (16.7 mg, 0.026 mmol) was added while the reaction was stirred vigorously. Vigorous stirring was continued for 15 min at room temperature, and then the reaction was diluted with EtOAc (40 mL) and washed with water and brine (20 mL each). The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography on silica gel (0 to 70% EtOAc/hexanes) to afford methyl {3-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-chloropyridin-3-yl]-4-methoxyphenyl}acetate. Rf=0.21 (25% EtOAc/hexanes). LCMS=617.4 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 6.92-7.83 (m, 8H), 4.88-5.68 (m, 2H), 3.58-4.19 (m, 10H), 0.63 (s, 3H).

Provenance & Evidence