Water → HCID 86710055, compound

Participants

Reaction Steps

6-Bromo-3-cyclohexyloxymethyl-2-isopropylimidazo[1,2-a]pyridine-7-carbonitrile (100 mg, 0.266 mmol) obtained in step 2 was dissolved in 1,4-dioxane-water (2/1) (1.5 mL), and the solution was stirred under heat and reflux for 3 hours after adding methylboronic acid (64.0 mg, 1.07 mmol), sodium carbonate (85.0 mg, 0.802 mmol), and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (44.0 mg, 0.0539 mmol). The reaction mixture was allowed to cool to room temperature, and, after adding water, the mixture was filtered through a Presep (registered trademark; diatomaceous earth, granular type M, 4.5 g/25 mL). The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=98/2) to give 3-cyclohexyloxymethyl-2-isopropyl-6-methylimidazo[1,2-a]pyridine-7-carbonitrile (51.4 mg, yield 62%).

Provenance & Evidence