Potassium Carbonate → HCID 71621380, compound

Participants

Reaction Steps

Under an argon atmosphere, 100 mg (purity 65%, 0.183 mmol) of 6-chloro-3-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-1,2,4-triazine-5-amine were suspended in 4 ml of absolute dioxane. 103 mg (0.731 mmol) of (5-fluoropyridin-3-yl)boronic acid and 25 mg (0.183 mmol) of potassium carbonate were added and argon was passed through the suspension for 10 min with stirring. Then, 3 mg (4.020 mol) of 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride were added and again argon was passed through the mixture for 1 min. The reaction mixture was stirred for 20 min in the microwave at 140° C. 5 mg (0.018 mmol) of tricyclohexylphosphine were added and the mixture was again stirred for 20 min in the microwave at 140° C. After cooling, the mixture was filtered over an Extrelut cartridge and after-washed with a mixture of dichloromethane/methanol (v/v=20:1). The filtrate was concentrated and the residue was purified by preparative HPLC (mobile phase: acetonitrile/water, gradient 20:80→100:0). 59 mg of the target compound were obtained (58% of theory).

Provenance & Evidence