Triethylamine → N-(5-Nitro-2-(phenylethynyl)phenyl)butyramide

Participants

Reaction Steps

To a solution of 2-butyramido-4-nitrophenyl trifluoromethanesulfonate (860 mg, 2.42 mmol) in dry acetonitrile (30 mL) under nitrogen was added tetrabutylammonium iodide (1.34 g, 3.62 mmol), tetrakis(triphenylphosphine)palladium(0) (280 mg, 0.24 mmol) and copper iodide (140 mg, 0.72 mmol). Triethylamine (6 mL) was then added, followed by phenyl acetylene (530 μL, 4.83 mmol). The resulting solution was stirred at room temperature for 2 h. Ammonium chloride was then added to quench the reaction, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated. The resulting solid was purified by column chromatography eluting using a gradient (hexanes to ethyl acetate) to afford 580 mg (78%) of the title compound.

Provenance & Evidence