Tetrahydrofuran → HCID 86710079, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 7-cyano-3-(4,4-difluorocyclohexylmethyl)-5-methylimidazo[1,2-a]pyridine-2-carboxylate (0.0410 g, 0.113 mmol) obtained in step 3 was dissolved in THF (1.0 mL), and the solution was stirred at −50° C. for 2 hours and then at 0° C. for 30 minutes after adding a THF solution of methylmagnesium bromide (1.1 mol/L) (0.446 mL, 0.500 mmol) at −50° C. Under ice-cooled condition, a saturated ammonium chloride aqueous solution was added to the reaction mixture, and 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 (heptane/ethyl acetate=80/20→65/35) to give 3-(4,4-difluorocyclohexylmethyl)-2-(2-hydroxypropan-2-yl)-5-methylimidazo[1,2-a]pyridine-7-carbonitrile (20.4 mg, yield 52%).

Provenance & Evidence