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

Participants

Reaction Steps

To a mixture of N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (50 mg, 0.152 mmol, 1 eq) and 1-(4-ethynylphenyl)-3-(3-methylphenyl)urea (57 mg, 1.5 eq) in anhydrous DMF (1 mL) under nitrogen atmosphere was added triethylamine (0.085 mL, 4 eq), bis(triphenylphosphine)palladium(II) dichloride (10.7 mg, 0.1 eq) and copper(I) iodide (5.8 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 solid residue was subject to a gradient column chromatography (from DCM to MeOH-DCM 1:9). The products' fractions were collected, concentrated, and the solid residue was triturated with EtOAc-Hex (6:1) to give N-(6-{[4-({[(3-methylphenyl)amino]carbonyl}amino)phenyl]ethynyl}imidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide as a brown solid upon filtration in amount of 46 mg.

Provenance & Evidence