131084-55-4

142078-36-2

131084-55-4

Using 2-(2-chloro-5-nitropyridin-4-yl)-N,N-dimethylvinyl-1-amine (221.2, 1.0 g, 4.4 mmol, 1.0 eq.) as starting material, it was dissolved in acetic acid (10 mL) at room temperature. Subsequently, iron powder (1.2 g, 22.0 mmol, 5.0 eq.) was added to this solution. The reaction mixture was heated to 90 °C and the reaction was stirred at this temperature for 2 hours. Upon completion of the reaction, sodium carbonate solution was slowly added to the reaction mixture to neutralize the reaction system, followed by extraction with ethyl acetate. All organic layers were combined, washed with brine solution to remove water-soluble impurities, and then the organic phase was dried with anhydrous sodium sulfate. After drying, the solvent was removed by concentration under reduced pressure to give the crude product. The crude product was further purified by column chromatography using a hexane solution of 30% ethyl acetate as eluent to give the target compound 5-chloro-1H-pyrrolo[2,3-c]pyridine (221.3, 0.65 g, 96.98% yield). Mass spectrometry (electrospray ionization): m/z 153.47 [M + H]+.