Sodium Iodide → 3-(5-Ethyl-2,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)benzonitrile

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Reaction Steps

A stirred mixture of 3-(5-ethyl-6-methoxy-2,4-dimethylpyridin-3-yl)benzonitrile (44 mg, 0.165 mmol), sodium iodide (50 mg, 0.33 mmol), chlorotrimethylsilane (58.4 μL, 0.33 mL) and acetonitrile (2 mL) is heated at reflux temperature for 3 hr. The cooled reaction mixture is diluted with water (10 mL) and extracted with dichloromethane. The extract is dried, filtered, concentrated and the residue is purified by chromatography eluting with cyclohexane-ethyl acetate then with dichloromethane-5% methanol. Product containing fractions are combined and concentrated to afford 3-(5-ethyl-2,4-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)benzonitrile (13 mg, 32%) as a beige solid. LC/MS: MS m/e=253 (M+H); RT 2.92 min.; 1H NMR (CDCl3, δ ppm) 7.69 (1H, d), 7.59 (1H, t), 7.45 (1H, s), 7.41 (1H, d), 2.63 (2H, q), 2.02 (3H, s), 1.84 (3H, s), 1.11 (3H, t).

Provenance & Evidence