Sodium Carbonate → HCID 69421875, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-pyridine-2,6-dicarboxylic acid diethyl ester (700 mg, 2.8 mmol), 5-chloro-2-methoxy-phenylboronic acid (630 mg, 3.4 mmol), palladium acetate (105 mg, 0.47 mmol) in ethylene glycol dimethyl ether (50 ml), degassed with argon, was added a solution of sodium carbonate (868 mg, 8.2 mmol) in water (5 ml) followed by triphenylphosphine (220 mg, 0.84 mmol). The mixture was stirred at 80° C. for 3 hours and filtered through a pad of celite under suction. The filtrate was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3 followed by 1:2) to give 4-(5-chloro-2-methoxy-phenyl)-pyridine-2,6-dicarboxylic acid diethyl ester (755 mg, 74% yield) as a white solid. 1H NMR (acetone-d6) δ 1.42 (t, 6H, J=7.1 Hz CH3), 3.92 (s, 3H, CH3), 4.45 (q, 4H, J=7.1 Hz, CH2), 7.27 (d, 1H, J=8.9 Hz, Ar), 7.52 (dd, 1H, J=8.8 Hz, J=2.7 Hz, Ar), 7.56 (d, 1H, J=2.7 Hz, Ar), 8.43 (s, 2H, Ar).

Provenance & Evidence