A mixture of ethyl 2-(2-chloropyridin-4-yl)acetate (44) (15.0 g, 75.0 mmol), tert-butylcarbamate (26.4 g, 225 mmol), Pd2(dba)3 (1.719 g, 1.88 mmol), caesium carbonate (36.7 g, 113 mmol) and Xantphos® (2.17 g, 3.76 mmol) in THF (100 mL) was purged with nitrogen and was then stirred at 65° C. for 8 hr. The mixture was cooled to RT and was diluted with water and extracted with ether. The ether extracts were combined and washed with water and brine and then dried (MgSO4), and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 330 g, 5-20% EtOAc in isohexane, gradient elution) then subjected to SCX capture and release to provide the title compound (45) (12.0 g, 51%): m/z 281 (M+H)+ (ES+).
