Sodium Carbonate → 5-(7-Ethyl-7H-imidazo[4,5-c]pyridazin-4-yl)-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-ol

Participants

Reaction Conditions

Reaction Steps

To a stirred solution 4-chloro-7-ethyl-7H-imidazo[4,5-c]pyridazine (Preparation 8, 80 mg, 0.44 mmol) and 4′-(ethylsulfonyl)-2′-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-2-ol (Preparation 89, 167 mg, 0.44 mmol) in dioxane (15 mL) and water (5 mL) was added sodium carbonate (106 mg, 1.0 mmol) and the reaction mixture was degassed before adding tetrakis(triphenylphosphine) palladium(0) (46 mg, 0.04 mmol). The reaction was heated to 100° C. for 18 hours. After this time the reaction was allowed to cool to room temperature, filtered through celite and the filtrate evaporated under reduced pressure. The crude was purified by silica gel column chromatography eluting with CH2Cl2:MeOH from 95:5 to 9:1 and then further purified by preparative HPLC to afford the title compound as colourless solid 11%, 19 mg.

Provenance & Evidence