To a slurry of (4R,5R)-5-(2,5-difluorophenyl)-4-(5-ethynylpyridin-3-yl)oxazolidin-2-one (50 mg, 0.167 mmol) in Triethylamine (Volume: 2 mL) was bubbled nitrogen for 20 min at which time 1-bromo-3,5-dichlorobenzene (49 mg, 0.22 mmol) was added with continued nitrogen bubbling for 5 min before adding bis(triphenylphosphine) palladium (II) chloride (8.8 mg, 0.012 mmol), triphenylphosphine (7.9 mg, 0.030 mmol), and copper (I) iodide (9.5 mg, 0.050 mmol) together in 1 portion. After 5 min additional nitrogen bubbling, the vessel was capped and placed in a 70° C. bath. After 18 h, the reaction was cooled, concentrated and diluted with methanol and purified via preparative liquid chromatography (Sunfire C18 OBD 30×100 mm 5 μm, A=95% H2O/5% Acetonitrile, B=95% Acetonitrile/5% H2O, Modifier 10 mM Ammonium Acetate, 0.00 min=20% B, 8.0 min=100% B, 13.0 min=100% B, Flow rate=40 mL/min) providing (4R,5R)-4-(5-((3,5-dichlorophenyl)ethynyl)pyridin-3-yl)-5-(2,5-difluorophenyl)oxazolidin-2-one (24 mg; 32%) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ ppm 8.78 (1H, d, J=1.83 Hz), 8.54 (1H, d, J=1.83 Hz), 7.79-7.97 (1H, m), 7.45 (2H, d, J=1.83 Hz), 7.39 (1H, t, J=1.83 Hz), 7.18-7.32 (2H, m), 7.00-7.18 (1H, m), 5.55 (1H, d, J=5.49 Hz), 5.40 (1H, s), 4.82 (1H, d, J=5.49 Hz), Mass Spectral Anal. Calcd. for [M+H]+ C22H12Cl2F2N2O2: 445.02. found 445.10.
