Dichloromethane → HCID 178487943, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a stirred suspension of 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (1.04 g) and 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (2.227 mmol, 0.972 g) in dioxane (18 mL) and 2 M aqueous potassium carbonate (10.6 mmol, 5.3 mL) under a nitrogen atmosphere was added 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride, complex with dichloromethane (0.212 mmol, 0.171 g) and the reaction mixture was heated by a preheated oil bath at 100° C. After two hours the reaction mixture was cooled to room temperature, water added and extracted with dichloromethane/methanol 9/1. The organic layer was separated and the water layer was extracted again with dichloromethane/methanol 9/1. The combined organic layers were washed with brine and dried (sodium sulfate) and evaporated to dryness to afford crude sample which was purified using column chromatography (silica gel; dichloromethane/methanol gradient (0 to 15% methanol)). Trituration with ethanol afforded 4-methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (0.44 g).

Herkunft & Nachweise