A mixture of 2-bromo-3-(4-(methylsulfonyl)-phenyl)-2-cyclopenten-1-one (700 mg, 2.2 mmol), Pd2 (dba)3 (170 mg, 0.18 mmol), and the total sample of 2-trimethylstannanyl-5-bromopyridine from Step 1 was dissolved in NMP (10 mL) and degassed. The resulting solution was heated to 100° C. for 3.5 h then cooled. The mixture was diluted with EtOAc, washed 2 times with 10% NH4OH and brine, dried over MgSO4, and concentrated. The residue was purified by flash chromatography (70% EtOAc/hexanes) followed by an EtOAc/Et2O swish to provide 110 mg of the title compound.
