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 (0.036 g, 0.04 mmol), and AsPh3 (0.098 g, 0.32 mmol) in NMP (5 mL) was added a degassed NMP solution (8 mL) of 2-trimethylstannanyl-5-chloropyridine (~4.0 mmol). The resulting mixture was heated to 60° C. for 16 h, then to 100° C. for a further 2 h. The mixture was then cooled to r.t., diluted with EtOAc, washed 2 times with 10% NH4OH and brine, dried over MgSO4, and concentrated to dryness. The residue was purified by flash chromatography (70% EtOAc/hexanes) followed by a CH2Cl2 /Et2O swish to provide 130 mg of the title compound.
