Potassium Carbonate → 4-(5-Bromo-2-((quinolin-2-ylthio)methyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

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Reaction Steps

A stirred solution of compound 1e (10 g, 30.45 mmol) and DIPEA (10.23 g, 79.30 mmol) in dichloromethane (200 mL) was cooled in an ice bath and MsCl (7.3 g, 63.48 mmol) was added dropwise. Upon complete addition, the reaction mixture was stirred for 3 h at room temperature and concentrated under reduced pressure. To the residue was added CH3CN (150 mL), followed by potassium carbonate (6.57 g, 47.6 mmol) and quinoline-2-thiol (5.62 g, 34.9 mmol). The resulting mixture was stirred overnight at 60° C. and allowed to cool to rt. Water (300 mL) was then added. The solids were collected by filtration. The crude product was recrystallized from DCM/ethyl ether (1:2 v/v) to obtain compound 78a as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C20H18BrN5OS: 457.1 (M+H). found: 457.0

Provenance & Evidence