3-(2-PYRIDYL)-3-OXOPROPANENITRILE

2524-52-9

75-05-8

54123-21-6

Preparation of Intermediate 35 [General Procedure 14]: Intermediate 34 (3 g, 19.6 mmol) and acetonitrile (0.8 mL, 19.6 mmol, 1 equiv) were dissolved in toluene (10 mL) under dry conditions. This solution was slowly added to a mixture of sodium hydride (784 mg, 19.6 mmol, 1 equiv, 60% mineral oil dispersion) pre-suspended in toluene (50 mL) and the reaction temperature was maintained at 65 °C. The reaction mixture was stirred continuously at 65°C for 16 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with ice-cold water (20 mL). The resulting solid was collected by filtration to afford Intermediate 35 (1.5 g, 53% yield) as a brown solid. The product was characterized by 1H NMR (CDCl3): δ 8.70 (d, J = 4.8Hz, 1H), 8.12 (d, J = 7.5Hz, 1H), 7.90-7.94 (m, 1H), 7.56-7.60 (m, 1H), 4.41 (s, 2H). Mass spectrometry analysis showed a molecular ion peak [M + H]+ of 147. Thin layer chromatography (TLC) analysis was performed with ethyl acetate as the unfolding agent and an Rf value of 0.40.