Nitrogen → (E)-Methyl 4-(8-morpholino-2-(2-(5,6,7,8-tetrahydroquinolin-2-yl)vinyl)imidazo[1,2-b]pyridazin-3-yl)benzoate

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Reaction Steps

A solution of compound 58b (0.70 g, 2.5 mmol) in THF (15 mL) was purged with N2. n-BuLi (2.5 M in hexane, 1.1 mL, 2.8 mmol) was added dropwise with stirring at rt and allowed to stir for 1 h. To the mixture was added compound 58c (0.70 g, 1.9 mmol). The resulting mixture was stirred overnight at rt, and quenched with saturated NH4Cl solution (100 mL). The resulting solution was extracted with DCM (3×100 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (EtOAc/petroleum ether (1:2 v/v)) to obtain compound 58d as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C29H29N5O3: 496.2 (M+H). Found: 496.2.

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