6-chloro-N-(4-methoxybenzyl)-N-phenyl-3-(2-(pyridin-4-yl)vinyl)imidazo[1,2-b]pyridazin-8-amine (75 mg, 0.16 mmol) from (1b), sodium tert-butoxide (22 mg, 0.22 mmol), trans-1,4-cyclohexanediamine (22 mg, 0.19 mmol) and acetato(2′-di-tert-butylphosphino-1,1′-biphenyl-2-yl)palladium (II) (7.4 mg, 0.01 mmole) were purged with argon for 15 min. then toluene (0.6 mL) was added via syringe. The contents were sonicated briefly and heated at 85° C. for 2 h. After cooling to room temperature, the mixture was partitioned between EtOAc (200 mL) and water (20 mL), and the organic layer was washed with water, brine, dried over MgSO4 and concentrated. The residue was purified by reverse phase preparative HPLC to provide N6-(trans-4-aminocyclohexyl)-N8-(4-methoxybenzyl)-N8-phenyl-3-(2-(pyridin-4-yl)vinyl)imidazo[1,2-b]pyridazine-6,8-diamine as a yellow solid (32 mg, 38%). LCMS[M+H]+ 546.
