Triphenylphosphine → HCID 69086079, compound

Participants

Reaction Conditions

Reaction Steps

To a 15 ml sealable vial was added a mixture of (4R,5R)-4-(5-bromo-2-fluoropyridin-3-yl)-5-(4-fluorophenyl)oxazolidin-2-one (270 mg, 0.760 mmol) in triethylamine (15 mL). To this suspension was added 3-ethynylpyridine (94 mg, 0.912 mmol), triphenylphosphine (59.8 mg, 0.228 mmol) and copper(I) iodide (2.90 mg, 0.015 mmol). The solution was degassed with nitrogen for 20 min, then bis(triphenylphosphine)palladium(II) chloride (10.67 mg, 0.015 mmol) was quickly added and the vial was sealed, heated to 90° C., and allowed to stir overnight. The next day the suspension had turned homogeneous and the reaction was cooled to room temperature and the solvent was evaporated in vacuo. The crude residue was purified by silica gel chromotagraphy 2% MeOH/98% CH2Cl2 affording (4R,5R)-4-(2-fluoro-5-(pyridin-3-ylethynyl)pyridin-3-yl)-5-(4-fluorophenyl)oxazolidin-2-one (210 mg, 0.540 mmol, 71.0% yield) 1H-NMR (CDCl3, 400 MHz) δ 8.82 (s, 1H), 8.64 (d, J=4.0, 1H), 8.44 (s, 1H), 8.14 (d, J=8.0, 1H), 7.86, (d, J=8.0, 1H), 7.44-7.40 (m, 2H), 7.38-7.36 (m, 1H), 7.19-7.15 (m, 2H), 5.64 (brs, 1H), 5.38 (d, J=4.0, 1H), 5.05 (d, J=4.0, 1H), LC/Mass spec. (Analytical HPLC method 2): RT=1.78 min. Mass=378.16 (MH)+.

Provenance & Evidence