Citric Acid → HCID 68964495, compound

Participants

Reaction Steps

To toluene 30 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 3.0 g were added indoline 2.1 mL, cesium carbonate 8.0 g,2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 0.29 g, tris(dibenzylideneacetone)dipalladium(0) 0.11 g and palladium acetate 55 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 3 hours and 30 minutes. After the reaction mixture was cooled to room temperature,2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 0.29 g, tris(dibenzylideneacetone)dipalladium(0) 0.11 g and palladium acetate 55 mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature, 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. Toluene was added to the obtained residue,dried over anhydrous magnesium sulfate after sequential washing with 1.0 mol/L hydrochloric acid and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-(indolin-1-yl)-2-nitrobenzoate 2.0 g of yellow solid.

Provenance & Evidence