GENERAL METHOD: Lithium bis(trimethylsilyl)amide (LiHMDS, 30 mmol) was rapidly added to a mixed solution of tetrahydrofuran (THF, 20 mL) and ethyl acetate (70 mmol) of ethyl isonicotinate (10 mmol) at -40°C, maintained at this temperature and stirred for 20 minutes. Upon completion of the reaction, the reaction mixture was quenched with acetic acid (50 mmol) and subsequently alkalized with 10% sodium bicarbonate (NaHCO3) solution. The reaction mixture was extracted with ethyl acetate (2 x 100 mL) and the organic layers were combined and washed sequentially with water and saturated saline. The organic layer was dried with anhydrous sodium sulfate (Na2SO4). Specific purification steps and characterization data are included for each compound.
