Dimethylformamide → HCID 67538520, compound

Participants

Reaction Conditions

Reaction Steps

DMF (20 mL) was added to a mixture of tert-butyl 6-bromo-1-cyclohexyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1.41 g), zinc cyanide (848 mg), and [1,1′-bis(diphenylphosphino)ferrocene]palladium chloride (535 mg), which was then purged with argon gas. Subsequently, tris(dibenzylideneacetone)dipalladium (458 mg) was added to the mixture which was then stirred at 120° C. under an argon atmosphere for 10 hours. Further, tris(dibenzylideneacetone)dipalladium (200 mg) was added thereto, followed by stirring for 10 hours. The reaction material was filtered through celite, and EtOAc and water were added to the filtrate. The organic layer was collected, washed with water and saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain tert-butyl 6-cyano-1-cyclohexyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (361 mg).

Provenance & Evidence