Sodium Carbonate → HCID 11462486, compound

Participants

Reaction Steps

A solution of Example 54A (259 mg, 1 mmol) and N-(6-bromo-3-pyridinyl)-N′-(3-methylphenyl)urea (367 mg, 1.2 mmol) (prepared from 2-amino-4-bromopyridine and m-tolylisocyanate following the procedure of Example 1E) in toluene (6 mL) and ethanol (6 mL) was degassed with N2 then treated sequentially with a solution of Na2CO3 (509 mg, 4.8 mmol) in water (3 mL) and tetrakis(triphenylphosphine)palladium (0) (208 mg, 0.187 mmol) and stirred at reflux overnight. The resulting suspension was cooled to room temperature, diluted with diethyl ether, and filtered. The filter cake was washed with water, diethyl ether, dichloromethane, ethyl acetate, and methanol. The combined filtrates were concentrated to give 51 mg of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 10.35 (s,1H), 9.58 (s,1H), 8.73 (s, 1H), 8.56 (s,1H), 8.06 (d, J=6 Hz, 1H), 7.56–7.81 (m, 4H), 7.3–7.46 (m, 2H), 7.20 (t, J=6 Hz, 1H), 6.85 (d, J=6 Hz, 1H), 4.56 (s, 2H), 2.31 (s,3H); MS (ESI(+)) m/e 359 (M+H)+.

Provenance & Evidence