To a stirred suspension of crude Chloride compound (3.0 g, 0.0095 mol), Boronic compound (1.6 g, 0.0095 mol) and 2 N Na2CO3 (14 ml) in toluene (45 ml) and EtOH (15 ml) was added a catalytic amount of Pd(PPh3)2Cl2 under nitrogen. The resulting mixture was refluxed overnight. TLC (EtOAc/petroleum ether 1 :3) indicated the reaction was complete. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated in vacuo to give a residue which was dissolved in dichloromethane (150 ml). After washing with water (50 ml x 3) and brine (50 ml x 3), the dichloromethane layer was dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product which was purified by column chromatography (silica gel, EtOAc/petroleum ether 1 :3) to afford compound 41 (2.1 g, 62%) as an off white solid.
Patent reference: WO2010038165 (Pfizer)