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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2239870Generated: October 27, 2026

Dimethylformamide → 6-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrile

https://huagongshe.com/reaction/2239870

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant3-bromo-6-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amineHCID 86611750—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
SolventEthyl AcetateHCID 8857—
Product6-Chloro-8-((4-methoxybenzyl)(phenyl)amino)imidazo[1,2-b]pyridazine-3-carbonitrileHCID 59314016—

Reaction Conditions

Temperature150 °C

Reaction Steps

A microwave vial was charged with 3-bromo-6-chloro-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine (220 mg, 0.49 mmol) from step 1a, zinc cyanide (34.8 mg, 0.3 mmol), Tris(dibenzylidenaceton)dipalladium(0) (22.7 mg, 0.025 mmol), 1,1′-Bis(diphenylphosphino)ferrocene (19.8 mg, 0.036 mmol) and DMF (2 mL). The resulting mixture was heated in a microwave for 15 min at 150° C. The solution was cooled, diluted with ethyl acetate, washed with saturated LiCl solution, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was purified silica gel chromatography (5% ethyl acetate/heptane) to provide 91 mg of 6-chloro-3-cyano-N-(4-methoxybenzyl)-N-phenylimidazo[1,2-b]pyridazin-8-amine

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07723336B2
Source datasetuspto-grants-2010_05
ORD IDord-c504c92da3c34bb3877d137c42715ce3
Source noteuspto-grants-2010_05