Tris(furan-2-yl)phosphane → (5R)-3-(3-Fluoro-4-(6-(5-hydroxymethyl-4,5-dihydroisoxazol-3-yl)pyridin-3-yl)phenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

(5R)-3-(3-Fluoro-4-iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (342 mg, 0.88 mM), {3-[5-(trimethylstannyl)pyridin-2-yl)-4,5-dihydroisoxazol-5-yl}methanol (300 mg, 0.88 mM), tris(dibenzylideneacetone) dipalladium (0)-chloroform adduct (91 mg, 0.088 mM, 0.1 equiv.) and tri-2-furylphosphine (41 mg, 0.176 mM, 0.2 equiv) were placed in a flask. The contents of the flask were degassed and placed under nitrogen. Anhydrous dioxane (5 ml) was added and the mixture was heated at 90° C. for 5 hours and then cooled to room temperature. Solvent was evaporated under reduced pressure and the residue was purified by chromatography (silica gel; elution with 5% methanol in dichloromethane) to give the title compound (170 mg).

Provenance & Evidence