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

Participants

Reaction Steps

A flask was charged with (4S,5R)-3-[(6-azetidin-1-yl-3-bromopyridin-2-yl)methyl]-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (134 mg, 0.249 mmol), methyl 3-[4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate (100 mg, 0.312 mmol), 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (8.11 mg, 0.012 mmol), and THF (3 mL). The reaction was degassed with N2 then 1M K2CO3 (3 mL, 3.00 mmol) was added. The reaction was stirred at room temperature for 45 min. The reaction was then diluted with ethyl acetate (20 mL), washed with water (2×15 mL) and brine (15 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (0 to 100% ethyl acetate/hexanes) to afford methyl 3-{3-[6-azetidin-1-yl-2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)pyridin-3-yl]-4-methoxyphenyl}propanoate. LCMS=652.2 (M+H)+. 1H NMR (CDCl3, 500 MHz) δ 7.84 (s, 1H), 7.72 (s, 2H), 7.29 (d, J=8.4 Hz, 1H), 7.15 (dd, J=8.3, 2.2 Hz, 1H), 6.97 (bs, 1H), 6.86 (d, J=8.5 Hz, 1H), 6.26 (d, J=8.4 Hz, 1H), 5.57 (bs, 1H), 4.75 (m, 1H), 4.33-3.95 (m, 6H), 3.75 (s, 3H), 3.64 (s, 3H), 2.91 (m, 2H), 2.62 (m, 2H), 2.40 (m, 2H), 0.66-0.59 (m, 3H).

Provenance & Evidence