Nitrogen → tert-Butyl 5-(8-morpholino-2-(2-(quinolin-2-yl)ethynyl)imidazo[1,2-b]pyridazin-3-yl)pyridin-2-ylcarbamate

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Reaction Conditions

Reaction Steps

A solution of compound 18b (0.50 g, 1.2 mmol) and tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-ylcarbamate (0.44 g, 1.4 mmol) in dioxane/water (4:1 v/v, 5 mL) was purged with N2. Dichloro(diphenylphosphinoferrocene)palladium (42 mg, 0.06 mmol) was then added, followed by solid Cs2CO3 (0.94 g, 2.9 mmol). The reaction mixture was stirred at 85° C. for 1 h under N2, and allowed to cool to rt. EtOAc (100 mL) was then added. The organic layer was washed with water (2×50 mL), and brine (100 mL), dried over Na2SO4, filtered and concentrated to give a residue which was purified by flash column chromatography on silica gel (0-40% EtOAc/heptanes) to give compound 38a as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C31H29N7O3: 548.2 (M+H). found: 548.1.

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