Cesium carbonate → 2-{4-[2-(3,4-Dichloro-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acid methyl ester

Participants

Reaction Steps

A mixture of 4-[2-(3,4-dichlorophenyl)-ethyl]benzenamine (600 mg, 2.25 mmol), 2-bromo-5-nitrobenzoic acid methyl ester (489 mg, 1.88 mmol), cesium carbonate (857 mg, 2.62 mmol), tris(dibenzylideneacetone-dipaladium(0) (51 mg, 0.056 mmol) and (S)-(2,2′-bis(di-p-tolylphosphino-1,1′-binaphthyl (98%, (S)-tol-BINAP) (58 mg, 0.085 mmol) (Ligand/Pd=1.5) in anhydrous toluene (16 mL) was heated to 100° C. for 12 hours under N2. After cooling, the reaction mixture was diluted with ether, filtered through celite and rinsed thoroughly with ether. The filtrate was evaporated to dryness to give a brown residue. Purification by flash chromatography (silica gel, 5% EtOAc/hexane) yielded 540 mg (1.21 mmol, 64%) of the desired product. mp 107-108° C.

Provenance & Evidence