Dichloromethane → HCID 178476589, compound

Participants

Reaction Conditions

Reaction Steps

To (cis)-4-(8-chloroimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (48.0 mmol, 14.09 g) in dry dioxane (275 ml) under a nitrogen atmosphere were added dry potasium carbonate (71.9 mmol, 9.94 g), trimethylboroxine (144 mmol, 20.03 ml, 50 wt % solution in tetrahydrofuran) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (4.80 mmol, 3.88 g) and the reaction mixture was stirred at 95° C. for one hour. The reaction mixture was cooled to room temperature, filtered over decalite, the filter rinsed with dioxane and the filtrate concentrated in vacuo. The residue was purified by column chromatography (silica gel; dichloromethane with gradient 0 to 6% of methanol) to give (cis)-4-(8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl acetate (12.8 g).

Provenance & Evidence