Sodium Carbonate → 4'-(Trifluoromethyl)-[1,1'-biphenyl]-3-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-iodoaniline in DME (40 mL) and water (20 mL), was added para-trifluoromethylphenyl boronic acid (2.6 g, 13.7 mmol) and sodium carbonate (2.5 g, 23.6 mmol). The apparatus was flushed with nitrogen prior to the addition of tetrakis (triphenylphosphine) palladium (0) (0.312 g, 0.27 mmol). The reaction mixture was stirred at 95° C. for 17 h under nitrogen, then allowed to cool to rt and the solvents removed in vacuo. The residue was partitioned between EtOAc (2×75 mL) and water (75 mL). The organic solution was dried (MgSO4) and the solvent was removed in vacuo. Purification by Biotage™ chromatography (90 g Silica column) eluted with 1:4 EtOAc:cyclohexane afforded the title compound as a white solid (1.33 g).

Provenance & Evidence