Dimethylacetamide → HCID 68483194, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 ml microwave vial was added 6-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (0.66 g, 1.8 mmol) from Example XXXI, step (1a), zinc cyanide (0.13 g, 1.1 mmol), Pd2(dba)3 (0.033 g, 0.036 mmol), 1,1′-bis(diphenylphosphino)-ferrocene [dppf] (0.040 g, 0.07 mmol), zinc dust (0.012 g, 0.18 mmol) and DMA (11.0 ml, 0.17 M). The reaction mixture was sealed and pump/purged 3× with nitrogen then heated in a microwave for 20 minutes at 150° C. Upon cooling, the suspension was diluted with ethyl acetate (50 ml) and filtered through a plug of celite. To the resulting solution was added 10% LiCl solution and the layers separated. The organic layer was washed two additional times with 10% LiCl solution, then brine (1×), dried over Na2SO4, filtered and concentrated in vacuo. This residue was purified on silica gel (ISCO—80 gram) using a 30-100% ethyl acetate/heptane gradient over 20 minutes. To provide 8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-6-carbonitrile (0.63 g, 98%). m/z=(357, M+1).

Provenance & Evidence