Citric Acid → HCID 67342384, compound

Participants

Reaction Steps

0.031 mL of indoline, 0.12 g of cesium carbonate, 1.7 mg of tris(dibenzylideneacetone)dipalladium(0), 0.8 mg of palladium acetate and 4.4 mg of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux 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 and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate -10:1] to obtain 77 mg of tert-butyl 2-(benzamido)-4-(indolin-1-yl)benzoate as yellow oil.

Provenance & Evidence