To a degassed r.t. solution of 2-bromo-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one (0.630 g, 2.0 mmol), Pd2 (dba)3 (0.037 g, 0.04 mmol), and AsPh3 (0.098 g, 0.32 mmol) in 5 mL NMP was added a degassed NMP solution (5 mL) of 3-trimethylstannanyl-5-chloropyridine (~2.0 mmol). The resulting mixture was heated to 60° C. for 16 h. The mixture was then cooled to r.t., diluted with EtOAc, washed with water and brine, dried over MgSO4, and concentrated to dryness. The residue was purified by flash chromatography (80% EtOAc/hexanes) followed by a CH2Cl2 /Et2O swish to provide 0.215 g of the title compound.
