反应详情

温度

100 °C

Methyl 6-hydroxybenzofuran-3-carboxylate (312 mg, 1.62 mmol) was dissolved in N,N-dimethylformamide (5 mL) then added 4-chloro-6,7-dimethoxyquinoline (451 mg, 2.02 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (77 mg, 0.162 mmol), palladium acetate (36 mg, 0.162 mmol) and potassium phosphate (687 mg, 3.24 mmol). The reaction mixture was stirred at 100° C. overnight. Additional palladium acetate (36 mg, 0.162 mmol) was added to the mixture and the heating was continued at 100° C. for 4 h. Additional 4-chloro-6,7-dimethoxyquinoline (181 mg, 0.812 mmol) and 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (77 mg, 0.162 mmol) were added to the mixture and heating at 100° C. was continued for 2 days. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The remaining orange oil was redissolved in toluene (5 mL) and DMF (1 mL) then added 4-chloro-6,7-dimethoxyquinoline (225 mg, 1.01 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (38 mg, 0.080 mmol), palladium acetate (18 mg, 0.080 mmol) and potassium phosphate (343 mg, 1.62 mmol). The reaction mixture was heated at 100° C. overnight and concentrated in vacuo. The remaining orange-black oil was purified by silica gel chromatography (1% to 2% methanol in dichloromethane) to afford methyl 6-(6,7-dimethoxyquinolin-4-yloxy)benzofuran-3-carboxylate as a light yellow solid. MS (ESI, pos. ion) m/z: 380.1 (M+1).

1. waitthe heating was continued at 100° C. for 4 h
2. temperatureheating at 100° C.
3. waitwas continued for 2 days
4. filtrationThe reaction mixture was filtered
5. concentrationthe filtrate was concentrated in vacuo
6. dissolutionThe remaining orange oil was redissolved in toluene (5 mL)
7. temperatureThe reaction mixture was heated at 100° C. overnight
8. concentrationconcentrated in vacuo
9. customThe remaining orange-black oil was purified by silica gel chromatography (1% to 2% methanol in dichloromethane)