Water → tert-Butyl 4-(5-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)pyridin-2-yl)piperazine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a suspension of compound 2a (200 mg, 0.643 mmol) and tert-butyl 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine-1-carboxylate (300 mg, 0.771 mmol) in 1,4-dioxane (10 mL) was added Na2CO3 solution (2 M, 1.61 mL, 3.21 mmol). The mixture was purged with Argon gas before the addition of PdCl2(dppf) (47.0 mg, 0.0643 mmol). The reaction mixture was stirred at 80° C. for 2 h. After cooling to rt, water (50 mL) was added and the mixture was extracted with DCM (2×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc/heptane (3:2 v/v) to obtain compound 19a as a yellow solid (276 mg, 87% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C25H31N7O4: 494.2 (M+H). Found 494.2.

Provenance & Evidence