反应详情

温度

110 °C

To toluene 3.0 mL solution of tert-butyl 2-amino-4-(indolin-1-yl)benzoate 0.12 g were added 1-bromo-3,4-methylenedioxybenzene 0.12 mL, cesium carbonate 0.26 g, tris(dibenzylideneacetone)dipalladium(0) 3.7 mg, palladium acetate 1.8 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg at room temperature, and it was stirred at 110° C. for 6 hours. Tris(dibenzylideneacetone)dipalladium(0) 3.7 mg, palladium acetate 1.8 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg were added at room temperature, and it was stirred at 110° C. for 18 hours 30 minutes. 1-Bromo-3,4-methylenedioxybenzene 0.12 mL, cesium carbonate 0.26 g, tris(dibenzylideneacetone)dipalladium(0) 3.7 mg, palladium acetate 1.8 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg were added to it, and it was stirred at 110° C. for 22 hours. After the reaction mixture was cooled to room temperature, tris(dibenzylideneacetone)dipalladium(0) 3.7 mg, palladium acetate 1.8 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 9.5 mg were added to it, and it was stirred at 110° C. for 20 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-((benzo-1,3-dioxol-5-yl)amino)-4-(indolin-1-yl)benzoate.

1. stirringit was stirred at 110° C. for 18 hours 30 minutes
2. stirringwas stirred at 110° C. for 22 hours
3. temperatureAfter the reaction mixture was cooled to room temperature
4. stirringwas stirred at 110° C. for 20 hours
5. temperatureAfter the reaction mixture was cooled to room temperature
6. filtrationinsoluble matter was filtrated
7. additionethyl acetate and 10% citric acid aqueous solution were added to it
8. customThe organic layer was separated
9. washafter washing with saturated sodium chloride aqueous solution
10. customthe solvent was removed under reduced pressure