2-(3-bromopyridin-2-yl)acetonitrile

13534-89-9

75-05-8

122851-60-9

General procedure for the synthesis of 3-bromo-2-pyridineacetonitrile from 2,3-dibromopyridine and acetonitrile: A tetrahydrofuran (THF, 8 mL) solution of acetonitrile (87 mg, 2.13 mmol) was slowly added to a THF solution of n-butyllithium (n-BuLi, 1.78 mL, 4.26 mmol) at -78 °C and stirred for 1 hour at -78 °C. Subsequently, a THF (2 mL) solution of 2,3-dibromopyridine (500 mg, 2.13 mmol) was slowly added at the same temperature. The reaction mixture was continued to be stirred at -78 °C for 1.5 h and then slowly warmed up to room temperature. Upon completion of the reaction, the reaction was quenched with saturated ammonium chloride (NH4Cl) solution and the organic phase was extracted with ethyl acetate (EA, 100 mL x 3). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate (Na2SO4) and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (HPLC) with the mobile phase of acetonitrile/water (containing 10 nM ammonium bicarbonate, NH4HCO3) to afford the target product 3-bromo-2-pyridineacetonitrile (110 mg, 22% yield) as a white solid. Liquid chromatography-mass spectrometry (LCMS) analysis showed [MH]+ = 197.