Dimethylformamide → HCID 18931449, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 0.13 g (0.45 mmol) of 4,4-dimethyl-3,4-dihydro-N-(4-methylphenyl)-7-ethynyl-2(1H)-quinolinone (Compound 20) and 0.29 g (1.0 mmol) of ethyl 4-iodobenzoate were added 2.9 g (4.0 mL, 29 mmol) of triethylamine, 2.0 mL of dimethylformamide, 0.019 g (0.10 mmol) of copper(I)iodide, and 0.067 g (0.10 mmol) of bis(triphenylphosphine)palladium(II) chloride, consecutively. The resulting mixture was heated at 50° C. for 16 hours. Thereafter methylene chloride was added and the reaction mixture was adsorbed onto silica gel. The mixture was purified by flash chromatography (15% ethyl acetate in hexanes) to give the title compound as an orange solid. PNMR (300 MHz, CDCl3) d 1.41 (3 H, t, J=7.1 Hz), 1.43 (6 H, s), 1.86 (2 H, t, J=6.0 Hz), 2.44 (3 H, s), 2.48 (2 H, s), 4.37 (2 H, q, J=7.1 Hz), 6.59 (1 H, d, J=1.5 Hz), 7.12 (2 H, d, J=8.3 Hz), 7.20-7.38 (4 H, m), 7.50 (2 H, d, J=8.1 Hz), 7.98 (2 H, d, J=8.1 Hz).

Provenance & Evidence