Triethylamine → N-(6-{[4-({[(3-methylphenyl)amino]carbonyl}amino)phenyl]ethynyl}imidazo[1,2-b]pyridazin-2-yl)acetamide

Participants

Reaction Steps

To a solution of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)acetamide (65 mg, 0.215 mmol, 1 eq) and 1-(4-ethynylphenyl)-3-(3-methylphenyl)urea (80.7 mg, 1.5 eq) in anhydrous DMF (2 mL) under nitrogen atmosphere was added triethylamine (0.12 mL, 4 eq), bis(triphenylphosphine)palladium(II) dichloride (15 mg, 0.1 eq) and copper(I) iodide (8.2 mg, 0.2 eq). After the reaction mixture was stirred at room temperature for 10 minutes, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper solution was decanted, concentrated, and the oily residue was wrapped with silica gel which was subject to a gradient column chromatography (from DCM to MeOH-DCM 1:9) to give N-(6-{[4-({[(3-methylphenyl)amino]carbonyl}amino)phenyl]ethynyl}imidazo[1,2-b]pyridazin-2-yl)acetamide as a brown solid in amount of 31 mg.

Provenance & Evidence