Citric Acid → HCID 68959346, compound

Participants

Reaction Steps

To toluene 3.0 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.10 g were added 1H-indole 48 mq, tripotassium phosphate 0.12 g, tris(dibenzylideneacetone)dipalladium(0) 8.0 mg, tri-tert-butylphosphine tetrafluoroborate 2.0 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.0 mg at room temperature, and it was heated and refluxed for 2 hours. After the reaction mixture was cooled to room temperature, tris(dibenzylideneacetone)dipalladium(0) 8.0 mg, tri-tert-butylphosphine tetrafluoroborate 2.0 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.0 mg were added to it, and it was heated and refluxed for 3 hours. After the reaction mixture was cooled to room temperature, tris(dibenzylideneacetone)dipalladium(0) 8.0 mg, tri-tert-butylphosphine tetrafluoroborate 2.0 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.0 mg were added to it, and it was heated and refluxed for 7 hours. After the reaction mixture was cooled to room temperature, toluene and 10% citric acid aqueous solution were added. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and 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=5:1] to give tert-butyl 2-(4-fluoroanilino)-4-(1H-indol-1-yl)benzoate.

Provenance & Evidence