Sodium Carbonate → HCID 3611076, compound

Participants

Reaction Conditions

Reaction Steps

A solution of phenylboronic acid (915 mg, 7.50 mmol) in methanol (15 mL) was added to a stirred solution of ethyl-2,6-dichloro-isonicotinate (750 mg, 3.41 mmol) and tetrakis-(triphenylphosphine)-palladium(0) (197 mg, 5 mol %) in toluene (60 mL). 2N sodium carbonate (3.41 mL, 6.82 mmol) was added and the reaction was heated to 90° C. (oil bath temp.) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (3×30 mL). The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MgSO4, filtered and concentrated in vacuo to yield the title compound as a white solid (941 mg, 91%); Rf: 0.5 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 8.18 (2H, s, ArH), 8.12 (4H, m, ArH), 7.42 (6H, m, ArH), 4.38 (2H, q, J=7 Hz, CH2O), 1.39 (2H, t, J=7 Hz, CH3)

Provenance & Evidence