A mixture of ethyl (4-{[(3-bromo-2-methylphenyl)(butyl)amino]methyl}-2-methylphenoxy)acetate (90 mg, 0.2 mmol), 4-methylphenylboronic acid (32 mg, 0.23 mmol), tetrakis(triphenylphosphine)palladium (0) (5 mg, 4.32 mmol), sodium carbonate (55 mg, 0.52 mmol) in 1,2-dimethoxyethane (10 mL) and water (5 mL) was heated at 90° C. for 18 h under nitrogen. The reaction mixture was cooled and the solvents removed in vacuo. Purification by SPE (C18, 10 g) eluting with 20 mL each of 5%, 10%, 30%, 50% acetonitrile/water, acetonitrile, MeOH. Further purification with SPE (amino propyl, 10 g), eluted with CH2Cl2 (40 mL), CHCl3 (20 mL), ether (20 mL), EtOAc (40 mL), MeOH (20 mL), 10% NH3/MeOH (40 mL) afforded the title compound as a colourless oil (50 mg).
