Nitrogen → 6-((6-(1-Ethoxyvinyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline

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A solution of 6-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methyl)quinoline (intermediate O) (50 mg, 0.169 mmol) and tributyl(1-ethoxyvinyl)stannane (0.06 mL, 0.178 mmol) in DMF (6 mL) was purged with N2 for 30 min and then Pd(PPh3)4 (9.77 mg, 0.0085 mmol) was added. The resulting solution was heated at 100° C. for 3 h. The reaction mixture was quenched with water, extracted with EtOAc three times. The organic layers were combined, washed with KF solution and brine, dried over Na2SO4. After concentration, the crude was used in the next step without further purification. LCMS (method A): [MH]+=332.1, tR=4.969 min.

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