4-tert-Butylphenylacetylene → Ethyl-6-(4-tert-butylphenylethynyl)nicotinate

Participants

Reaction Steps

A mixture of 477.7 mg (3.02 mmol) of 4-tertbutylphenylethyne (Compound 19), 556.5 mg (3.01 mmol) of ethyl-6-chloronicotinate (Compound 54), 27.8 mg (0.15 mmol) of cuprous iodide, 58.7 mg (0.08 mmol) of bis(triphenylphosphine)palladium (II) chloride and 2 ml of triethylamine was degassed under nitrogen and then stirred under nitrogen at room temperature for 40 hours. The mixture was then heated at 65 degrees C. for 12 hours, cooled to room temperature and the excess triethylamine removed under vacuum. The residue was taken up in water and extracted with ether. The solvent was then removed in-vacuo and the residue purified by flash chromatography (silica 5% ethyl acetate in hexane) to give the title compound as a pale brown solid. PMR (CDCl3) : & 1.33 (9H, s), 1.42 (3H, t, J-7.1 Hz); 4.42 (2H, q, J-7.1 Hz), 7.40 (2H, d, J-8.4 Hz), 7.53-7.61 (3H, m), 8.28 (1H, dd, J-8.1 Hz, 2.0 Hz), 9.20 (1H, d, J-2.0 Hz).

Provenance & Evidence