Stannane, tributyl(1-ethoxyethenyl)- → 6-(1-Ethoxy-vinyl)-3-(1-methyl-1H-indazol-5-ylmethyl)-imidazo[1,2-b]pyridazine

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Reaction Conditions

Reaction Steps

A suspension of 6-chloro-3-((1-methyl-1H-indazol-5-yl)methyl)imidazo[1,2-b]pyridazine (180.0 mg, 36% purity, 0.22 mmol), tributyl(1-ethoxyvinyl)stannane (94 mg, 0.26 mmol) and Pd(PPh3)4 (25.1 mg, 0.02 mmol) in 10 mL of DMF was flushed with nitrogen, then heated at 110° C. and stirred overnight. Solvent was removed under reduced pressure; the residue was diluted with DCM, washed sequentially with aqueous KF and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (DCM:MeOH=20:1) to give the title compound containing some triphenylphosphine oxide impurity but used in the next step without further purification (49 mg, 47%, 70% purity). LCMS (method A): [MH]+=334, tR=5.71 min.

Provenance & Evidence