3-Methyl-5-(tributylstannyl)isoxazole → (5R)-5-((1H-1,2,3-triazol-1-yl)methyl)-3-(3-fluoro-4-(3-methylisoxazol-5-yl)phenyl)oxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A suspension of (5R)-3-(3-fluoro-4-iodophenyl)-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Intermediate 6, 582 mg, 1.50 mmol) in 1,4-dioxane (14 ml) was placed under argon. Bis(triphenylphospine)palladium (II) chloride (42 mg, 0.060 mmol) was added, followed by the dropwise addition of 5-(tributylstannyl)-3-methylisoxazole (Sakamoto, T. et al; Tetrahedron, 1991, 47, 5111–5118; 0.84 g, 2.25 mmol) in 1,4-dioxane (1 ml). The mixture was heated at 100° C. After approximately 16 hours, the solution was concentrated under vacuum. The crude material was dissolved in acetonitrile and washed with hexanes (3×). The acetonitrile phase was concentrated under vacuum. Purification by chromatography on silica gel using EtOAc, followed by recrystallization from EtOAc/MeOH gave 256 mg of the title product.

Provenance & Evidence