Cesium carbonate → Methyl 5-(6-(3-ethylureido)pyridin-3-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate

Participants

Reaction Steps

A solution of N-ethyl-N′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)urea (Intermediate 1, 200 mg, 0.69 mmol), methyl 5-iodo-2-oxo-1,2-dihydro-3-pyridinecarboxylate (174 mg, 0.62 mmol), Tetrakispalladium (72.2 mg, 0.06 mmol), and cesium carbonate (224 mg, 0.69 mmol) in dioxane (4 mL) and water (1.000 mL) was heated to 100° C. in microwave for 1 h. The reaction mixture was filtered through Celite and washed with methanol. The resulting solution was concentrated under reduced pressure to give a yellow solid. The solid was triturated with acetone, then collected by filtration and added to hot acetone/water. The solution was cooled to room temperature, and the solid that formed was collected by filtration and placed under high vacuum to remove residual solvent (58 mg). MS (ESP): 317 (M+H+) for C15H16N4O4.

Provenance & Evidence