Triethylamine → HCID 58525563, compound

Participants

Reaction Steps

To a mixture of methyl 6-hydroxyquinoline-3-carboxylate (0.142 g, 0.699 mmol) in methylene chloride (7 mL) and triethylamine (0.974 mL, 6.99 mmol) were added phenylboronic acid (197 mg, 1.62 mmol), copper(II) acetate (294 mg, 1.62 mmol) and 4 Å molecular sieves (approx 200 mg). The mixture was stirred at room temperature over night. Solids were removed from the reaction mixture by filtration and the filter pad was washed thoroughly with ethyl acetate. The filtrate was washed twice with ammonium hydroxide solution and then brine. The extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography (hexanes to 50/50 hexanes/ethyl acetate gradient) to afford Int-17 (0.143 g, 73%). LC-MS: (FA) ES+280; 1H NMR (400 MHz, d6-DMSO) δ ppm 9.22 (d, J=2.1 Hz, 1H), 8.95 (d, J=1.8 Hz, 1H), 8.13 (d, J=8.8 Hz, 1H), 7.70-7.66 (m, 2H), 7.49-7.43 (m, 2H), 7.23 (tt, J=7.5, 7.5, 1.1, 1.1 Hz, 1H), 7.17-7.13 (m, 2H), 3.93 (s, 3H).

Provenance & Evidence