Water → 4-(5-Bromo-2-(quinolin-2-ylethynyl)imidazo[1,2-a]pyrazin-8-yl)morpholine

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Reaction Steps

To a stirred solution of compound 80a (200 mg, 0.7 mmol) and 2-bromoquinoline (0.800 mg, 4 mmol) in dry DMF (5 mL) and DIEA (0.7 mL, 4 mmol) under an Argon gas atmosphere, CuI (12 mg, 0.06 mmol) and (Ph3P)2PdCl2 (46 mg, 0.06 mmol) were added. The reaction was stirred at rt overnight, poured into water (50 mL) and extracted with DCM (3×30 mL). The combined organic extracts were washed with water (20 mL), brine (2×20 mL), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (0-50% EtOAc/heptanes) to give compound 80b as an off-white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C21H16BrN5O: 434.0 (M+H). found: 434.2.

Provenance & Evidence