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

Participants

Reaction Conditions

Reaction Steps

(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 2, 2.08 g, 5.20 mmol) was dissolved in anhydrous 1,4-dioxane (10 ml) and degassed and placed under argon. Bis(triphenylphospine)palladium(II) chloride (0.145 g, 0.210 mmol) was added followed by dropwise addition of 5-(tributylstannyl)-3-methylisoxazole (2.41 g, 6.50 mmol) (Sakamoto, T. et al., Tetrahedron, 47, 28, 5111–5118) in 1,4-dioxane (2 ml). The reaction was degassed and heated at 100° C. for 48 hours. The solvent was removed under vacuum and the residue was dissolved in acetonitrile and washed with hexanes. The acetonitrile layer was concentrated to give a yellow solid (1.64 g) that was adsorbed onto silica gel and purified by flash chromatography using 10–20% acetone/dichloromethane. Relevant fractions were concentrated to give an off-white solid (1.50 g).

Provenance & Evidence