azd4635

697739-22-3

1321517-59-2

1321514-06-0

6-Bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine (1 mole-equivalent), 2-chloro-6-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1 mole-equivalent), and K2CO3 (1.5 mole-equivalent) were used as raw materials suspended in a solvent mixture of 1,4-dioxane and water (v/v ratio 2 :1; 10 mL solvent/g 6-bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine). The mixture was degassed and dichlorobis[bis(4-dimethylaminophenyl)phosphino]palladium(II) (2 mol%) was added as a catalyst, and the reaction was heated and refluxed until complete consumption of 6-bromo-5-(4-fluorophenyl)-1,2,4-triazin-3-amine was confirmed by LCMS monitoring. Upon completion of the reaction, the reaction mixture was cooled, diluted with water, extracted with dichloromethane and the organic phase was separated by a phase separator. The organic phase was concentrated under reduced pressure and purified by gradient fast chromatography using a mixture of ethyl acetate and hexane solvents as eluent to give the final target product 6-(2-chloro-6-methylpyridin-4-yl)-5-(4-fluorophenyl)-1,2,4-triazin-3-amine in 61% yield.