Cesium carbonate → 2-[6-(5-Bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-pyridin-3-yl]-2-methyl-propionic acid methyl ester

Participants

Reaction Steps

2-(6-Amino-pyridin-3-yl)-2-methyl-propionic acid methyl ester (1.5 g, 7.7 mmol), 3,5- dibromo-1-methyl-1H-pyridin-2-one (2.05 g, 7.7 mmol), cesium carbonate (7.53 g, 23.1 mmol), bis(dibenzylideneacetone)palladium (353 mg, 0.385 mmol), and Xantphos (446 mg, 0.77 mmol) were added to a round bottom flask and the flask was purged with nitrogen. Degassed dioxane (50 ml) was added through a syringe. The reaction mixture was heated at 100 degrees centigrade overnight. The reaction mixture was filtered through celite and concentrated. The crude product was purified by flash chromatography using a gradient of 0% to 50% ethyl acetate in hexanes to give 1.8 g (62%) of 2-[6-(5-bromo-1-methyl-2-oxo-1,2-dihydro-pyridin-3-ylamino)-pyridin-3-yl]-2-methyl-propionic acid methyl ester.

Provenance & Evidence