Potassium Carbonate → HCID 60026537, compound

Participants

Reaction Steps

To a mixture of 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-1, 1,1-trifluoro-4-methylpentan-2-one (1.00 g, 2.8 mmol), pyrimidine-5-boronic acid (529 mg, 4.3 mmol) and potassium carbonate (787 mg) in a sealed tube was added 20 mL of MeOH-DME-DMF (3:2:1). After stirring at room temperature for 10 minutes, tetrakis(triphenylphosphine)palladium(0) (329 mg) was added and the reaction mixture was heated at 120° C. for 40 minutes. After cooling to room temperature, the crude mixture was filtered through a cotton plug with the aid of ethyl acetate. The filtrate was concentrated in vacuo to remove most of the methanol, redissolved in 160 mL of ethyl acetate, and washed with 80 mL of aqueous 1 N sodium hydroxide solution, 80 mL of water, and 80 mL of brine respectively. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Purification by column chromatography with 20% to 30% ethyl acetate-hexanes afforded 620 mg (62% yield) of the title compound.

Provenance & Evidence