Sodium Carbonate → Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

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Reaction Steps

Methyl 5-bromo-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate (80 mg), 2-chlorophenylboronic acid (58 mg), palladium tetrakis(triphenylphosphine) (22 mg) and 1M aqueous sodium carbonate (450 μL) were mixed in ethylene glycol dimethyl ether (2 mL), degassed with argon and then heated to reflux for 90 min. The cooled reaction mixture was diluted with ether, filtered through celite and concentrated. The residue was purified by silica gel chromatography eluting with 70% hexane:30% ethyl acetate to give the title compound. 1H NMR (500 MHz, CDCl3): δ 7.82 (d, J=1.4 Hz, 1H); 7.65-7.39 (m, 8H); 7.23 (s, 1H); 6.82 (d, J=9.9 Hz, 1H), 3.90 (s, 3H). Mass spectrum: m/z 458 (M+H).

Provenance & Evidence