1-Ethoxy-4-ethynylbenzene → 2-[(4-Ethoxyphenyl)ethynyl]-5-(methoxymethoxy)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-5-(methoxymethoxy)pyridine (2.50 g, 11.5 mmol), 1-ethoxy-4-ethynylbenzene (2.57 mL, 17.2 mmol) and copper(I) iodide (220 mg, 1.15 mmol) in a mixed solvent of THF-triethylamine (20 ml-10 mL) was added bis(triphenylphosphine)palladium(II) chloride (807 mg, 1.15 mmol), and the mixture was stirred under an argon stream at 60° C. for 15 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 3:7) to give the title compound (3.21 g, yield 98%) as a yellow solid.

Provenance & Evidence