Potassium Carbonate → HCID 45376866, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloromethyl-pyridine hydrochloride (0.59 g 3.6 mmol) was added to a mixture of (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-(3-hydroxy-phenyl)-acrylamide (0.39 g, 1.2 mmol) and potassium carbonate (0.83 g, 6.0 mmol) in dry DMF (5 mL) at RT. After stirring at 40° C. for 5 hrs, the resulting mixture was poured into ice, and the resulting precipitate was filtered, washed with water and dried. The resulting raw material was taken up, without further purification, with a 3N methanolic solution of hydrochloric acid (5 mL-15 mmols) and stirred at RT for 2.5 hrs, concentrated under reduced pressure, taken up with solvent an re-evaporated (3 times with MeOH and once with acetone) to give a residue that, after neutralization, was purified by silica gel column chromatography (eluant DCM/MeOH 98/2) to obtain 50 mg of the title (E)-3-(3-hydroxy-4-methoxy-phenyl)-N-[3-(pyridin-3-ylmethoxy)-phenyl]-acrylamide.

Provenance & Evidence