Dimethylformamide → HCID 69085234, compound

Participants

Reaction Steps

(4R,5R)-4-(6-chloropyridin-3-yl)-5-(3-fluorophenyl)oxazolidin-2-one (52 mg; 0.18 mmol), ethynylbenzene (20.0 mg, 0.19 mmol), bis(triphenylphosphine) palladium (II) chloride (6.2 mg, 8.88 μmol), triphenylphosphine (9.3 mg, 0.036 mmol), and copper (I) iodide (1.6 mg, 8.88 μmol) were combined in a microwave vial. dimethylformamide (0.5 mL) and diisopropylethylamine (1.5 mL) were added resulting in a biphasic mixture. Nitrogen was bubbled through the vessel for 10 min, the vessel was capped and the reaction was run at 120° C. for 25 min on a Biotage microwave reactor. The diisopropylethylamine removed in vacuo, the remaining solution was diluted with methanol and the solution was 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, 10.0 min=100% B, 15.0 min=100% B, Flow rate=40 mL/min) providing 31 mg (48%) (4R,5R)-5-(3-fluorophenyl)-4-(6-(phenylethynyl)pyridin-3-yl)oxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ ppm 8.49 (1H, d, J=2.14 Hz), 7.75 (1H, dd, J=8.24, 2.44 Hz), 7.56-7.66 (3H, m), 7.32-7.46 (4H, m), 7.11 (1H, td, J=8.39, 2.44 Hz), 6.98-7.09 (2H, m), 5.34 (1H, s), 5.28 (1H, d, J=7.63 Hz), 4.79 (1H, d, J=7.32 Hz). Mass Spectral Anal. Calcd. for [M+H]+ C22H15FN2O2: 359.1. found 359.3.

Provenance & Evidence