Sodium Carbonate → HCID 89589901, compound

Participants

Reaction Steps

9-chloro-3-methyl-1-(3-(trifluoromethyl)phenyl)-3,4-dihydropyrimido[5,4-c][1,5]naphthyridin-2(1H)-one (314 mg, 0.80 mmol), tetrakis(triphenylphosphine) palladium (15 mg, 0.013 mmol) and 2N aqueous sodium carbonate solution (1.3 mL) were added sequentially to a solution of N-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)acetamide (225 mg, 0.858 mmol) in 1,4-dioxane (15 mL), and reacted under nitrogen at 90° C. for 16 h, cooled to room temperature, filtered, the organic layer was concentrated under reduced pressure, dissolved in 50 mL of dichloromethane, washed sequentially with water and saturated brine, dried over anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (ethyl acetate) to give 267 mg of the product.

Provenance & Evidence