Dichloromethane → 2'-tert-butyl-1-(3-methoxyisoquinoline-6-carbonyl)-4',6'-dihydrospiro[piperidine-4,5'-pyrazolo[3,4-c]pyridin]-7'(2'H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-3-methoxyisoquinoline (Intermediate 43, 89.9 mg, 0.378 mmol) in 1,4-dioxane (6 mL) was added 2′-tert-butyl-4′,6′-dihydrospiro[piperidine-4,5′-pyrazolo[3,4-c]pyridin]-7′(2′H)-one hydrochloride salt (Intermediate 4, 244 mg, 0.727 mmol) and sodium acetate (130 mg, 1.5 mmol). Nitrogen gas was bubbled through the mixture for 15 minutes. Then added [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (102 mg, 0.125 mmol), capped the reaction vessel and bubbled through carbon monoxide gas for 5 minutes. The reaction was then heated to 80° C. for 18 hours. The reaction was cooled to room temperature and diluted with ethyl acetate. The mixture was filtered through Celite and the filtrate was concentrated. Purification by reversed-phase HPLC gave the title compound. +ESI (M+H) 448.1; HPLC retention time 2.26 minutes (Method A).

Provenance & Evidence