Sodium Carbonate → HCID 59574762, compound

Participants

Reaction Conditions

Reaction Steps

2-[(3-Chloropyridazin-4-yl)methyl]-1H-isoindole-1,3(2H)-dione (137 mg, 0.5 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (252 mg, 0.28 mL, 1.5 mmol), tetrakis(triphenylphosphine)palladium (57.8 mg, 0.05 mmol) and sodium carbonate (106 mg, 2.00 mmol) were mixed with water (0.2 mL) and 1,4-dioxane (0.9 mL) and stirred at 110° C. for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and the solvent was removed by vacuum distillation. The resulting residue was mixed with 4 M hydrogen chloride/1,4-dioxane (5 mL) and stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was mixed with water and extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2). The obtained colorless solid (76 mg) and 10% palladium-carbon (50 wt %, 100 mg) were stirred in methanol (5 mL) under hydrogen atmosphere (1 atm) at room temperature for 16 hours. After filtering through celite, the filtrate was evaporated under reduce pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/2) to give the desired product (76.3 mg, 54% yield).

Provenance & Evidence