Cesium carbonate → 2-(3-(9-Ethyl-9H-imidazo[4,5-c]pyridazin-6-yl)phenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine

Participants

Reaction Steps

A room temperature solution of 2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-2,3-dihydro-1H-1,3-diaza-2-boraphenalene (Preparation 61, 7.8 g, 21.1 mmol), 4-chloro-7-ethyl-7H-imidazo[4,5-c]pyridazine (Preparation 8, 2.6 g, 14.1 mmol) and cesium carbonate (13.8 g, 42.3 mmol) in dioxane (160 mL) and water (13 mL) was degassed. 1,1′-bis(di-tert-butylphosphino) ferrocene palladium dichloride (0.91 g, 1.4 mmol) was then added in one portion and the reaction mixture was again purged with nitrogen gas three times. The resultant solution was then stirred at reflux for 16 hours. The reaction mixture was cooled to room temperature then filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with CH2Cl2:MeOH, 50:1 to afford the title compound as a yellow solid in 83.6% yield.

Provenance & Evidence