tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylate → Tert-butyl 4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)prop-2-ynyl]piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 4-(prop-2-ynyl)piperazine-1-carboxylate (0.449 g, 2.00 mmol) in triethylamine (12 mL) was added with 7-iodo-6-methoxybenzofuran-3(2H)-one (0.580 g, 2.00 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.141 g, 0.200 mmol) and copper(I) iodide (0.0381 g, 0.200 mmol), and the mixture was stirred at 50° C. for 4 hours. The reaction mixture was concentrated, then the solid was suspended in a mixed solvent of 50% ethyl acetate in hexane, and the suspension was filtered. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain tert-butyl 4-[3-(6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl)prop-2-ynyl]piperazine-1-carboxylate (0.473 g, 61%).

Provenance & Evidence