100367-55-3

4487-59-6

143-33-9

544-92-3

100367-55-3

Synthesis of Compound E: Copper(I) cyanide (662 mg, 7.34 mmol) and sodium cyanide (242 mg, 4.93 mmol) were dissolved in N,N-dimethylformamide (7.5 mL) and stirred at 150 °C for 25 min. Subsequently, a solution of 2-bromo-5-nitropyridine (113 mg, 0.700 mmol) dissolved in N,N-dimethylformamide (2.5 mL) (pre-dissolved completely at 100 °C) was added to the above mixture and the reaction was continued to be stirred at 150 °C for 100 min. The progress of the reaction was monitored by TLC (unfolding agent: ethyl acetate/hexane = 1:3). Upon completion of the reaction, the reaction was quenched by the addition of 10 mL of aqueous 1M potassium dihydrogen phosphate and extracted with ethyl acetate (50 mL x 3). The organic phases were combined and washed sequentially with water (100 mL) and saturated saline (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered, and concentrated under reduced pressure to remove the solvent. The product was purified by fast column chromatography (eluent: ethyl acetate/hexane = 1:7→1:3) to afford 2-cyano-5-nitropyridine E (624 mg, 4.19 mmol) as a yellow oil in 85% yield.1H NMR (300 MHz, CDCl3) δ: 9.54 (dd, 1H, J = 2.5, 0.7 Hz, Py-H), 8.68 (dd, 1H, J = 8.4, 2.5 Hz, Py-H), 7.98 (dd, 1H, J = 8.4, 0.7 Hz, Py-H).