Cesium carbonate → 4-(5,8,8-Trimethyl-7,8-dihydro-naphthalen-2-yl-amino)-benzoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

General Procedure L To a solution of 5,8,8-trimethyl-7,8-dihydro-naphthalen-2-yl-amine (Compound 64, 0.33 g, 1.8 mmol) and ethyl 4-bromobenzoate (0.52 g, 2.3 mmol) in 10.0 mL of toluene while stirring under argon were added cesium carbonate (0.89 g, 2.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3, 33 mg, 0.04 mmol) and bis(diphenylphosphino)-1,1′-binaphthyl (BINAP, 47 mg, 0.08 mmol) consecutively. The reaction was then heated at 100° C. for 24 h. The reaction was then cooled to room temperature, diluted with water and extracted 2 times with ethyl ether. The combined organic extracts were washed with brine, dried over MgSO4, filtered, and the solvents were removed in vacuo. The crude product was purified by silica gel chromatography (10% ethyl acetate in hexanes) to give the title compound as a yellow solid.

Provenance & Evidence