Tetrahydrofuran → (5R)-3-{3-Fluoro-4-[(trimethylsilyl)ethynyl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Participants

Reaction Steps

(5R)-3-(3-Fluoro-4-iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Intermediate 6, 0.50 g, 1.3 mmol), tris(dibenzylideneacetone)dipalladium (0) (24 mg, 0.026 mmol), tri-2-furylphosphine (12 mg, 0.05 mmol), and copper iodide (5.0 mg, 0.013 mmol) were combined in a flask and degassed. Tetrahydrofuran (7.5 ml), triethylamine (0.54 g, 5.4 mmol) and a minimal amount of 1-methyl-2-pyrrolidinone (1.5 ml) were added to obtain a brown solution. (Trimethylsilyl)acetylene (0.18 g, 1.8 mmol) was added and the reaction was stirred at room temperature overnight. The solution was adsorbed onto silica gel and chromatographed eluting with ethyl acetate to give the title compound as a brown oil (1.2 g) (contains 1-methyl-2-pyrrolidinone).

Provenance & Evidence