1,2-Dimethoxyethane → HCID 86699332, compound

Participants

Reaction Conditions

Reaction Steps

A dried flask equipped with a reflux condenser and a nitrogen line was charged with methyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate (200 mg, 0.784 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (180 mg, 0.869 mmol) and PdCl2(dppf)dichloromethane adduct (64 mg, 0.078 mmol). To the flask was added 3 mL 1,2-dimethoxyethane containing 1% absolute ethanol, followed by addition of triethylamine (0.22 mL, 1.57 mmol). The flask was degassed under nitrogen and heated at 85° C. for 10 hours. The reaction mixture was allowed to cool to ambient temperature and then diluted with water. The resulting suspension was extracted with DCM. The combined organic extracts were dried over anhydrous sodium sulfate, and concentrated to afford the crude product. The crude product was subjected to preparative thin-layer chromatography on silica with 4% MeOH/DCM as eluent to afford 47.4 mg of pure, desired product as a pale yellow solid.

Provenance & Evidence