Phosphine, tris(4-methoxyphenyl)- → HCID 10194990, compound

Participants

Reaction Conditions

Reaction Steps

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-(2,2-dibromoethenyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 25) (0.3 g, 0.52 mmol), allyl tributyl tin (160 μl, 0.55 mmol) and tris(4-methoxyphenyl)phosphine (28 mg, 0.08 mmol) were dissolved in DMF (2.5 ml). Diisopropylethyl amine (136 μl, 0.78 mmol) was added, the reaction mixture was flushed with argon and tris(dibenzylideneacetone)dipalladium (0) (15 mg, 0.01 mmol) was added. The mixture was heated to 80° C. for 10 hours under argon. It was diluted with ethyl acetate, washed with phosphate buffer (pH 7), saturated aqueous potassium fluoride solution and with water and dried over sodium sulfate. Chromatography on silica gel with chloroform/methanol (15:1) gave 32 mg (14%) of the title compound as a colourless solid.

Provenance & Evidence