A mixture of 3-(3-fluorobenzyl)-N-(4-(trimethylsilyl)but-3-ynyl)benzamide (0.130 g; 0.365 mmol), 2,4-dichloro-6-iodoaniline (0.127 g; 0.441 mmol), palladium (II) acetate (0.016 g; 0.073 mmol) and sodium carbonate (0.195 g; 1.84 mmol) in DMF (8 mL) was heated at 100° C. for 18 hours in a sealed tube and concentrated under reduced pressure. The residue was suspended in brine and extracted with dichloromethane (2×100 mL). The organic layer was dried and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel (eluent 2 to 10% ethyl acetate in dichloromethane) to furnish 0.045 g (23%) of N-(2-(5,7-dichloro-2-(trimethylsilyl)-1H-indol-3-yl)ethyl)-3-(3-fluorobenzyl)benzamide.
