To a microwave vessel was added 3-bromo-6-(6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylmethyl)-quinoline (500 mg, 1.41 mmol, 1 equiv), vinyl boronic acid (299 uL, 1.76 mmol, 1.25 equiv), K2CO3 (390 mg, 2.82 mmol, 2.0 equiv) followed by 1,4-dioxane (10 mL) and water (5 mL). The solution was degassed with nitrogen for 10 min and then dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (51 mg, 0.07 mmol, 0.05 equiv) was added. The microwave vessel was capped and reacted in a microwave reactor at 130° C. for 30 min. The microwave vessel was cooled and then the mixture was extracted into dichloromethane and washed with water. The volatiles were removed in vacuo and the residue absorbed onto silica gel and purified by flash chromatography (SiO2, CH2Cl2:CH3OH 100:0-80:20) to obtain the title compound as a brown oil (35% yield). Analytical data presented in Table 1.
