Dimethyl Sulfoxide → HCID 60147144, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-benzyl-3-[4′-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)phenyl]-benzofuran (500 mg, 1.22 mmol) in anhyd DMSO (5 mL) was added to a stirred suspension of 5-[2-(4-bromophenyl)-2-oxoethyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione (436 mg, 1.22 mmol) and tripotassium phosphate (1.04 g, 4.88 mmol) in anhyd DMSO (5 mL). [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)-DCM complex (100 mg, 0.12 mmol) was added as a solid, and the resulting suspension was heated to 80° C. for 2 h. The reaction mixture was cooled to room temperature, diluted with diethyl ether (150 mL), washed with water (2×50 mL), sat'd aq NaCl (3×50 mL), dried over anhyd MgSO4, filtered and concentrated in vacuo. Purification by flash column chromatography (50-60% ethyl acetate in heptane) afforded the title compound as an off-white solid (502 mg).

Provenance & Evidence