Sodium Iodide → 3-ethyl-6-methyl-5-(1,2,4-oxadiazol-5-yl)-1H-pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(1,2,4-oxadiazol-5-yl)pyridine (36 mg, 0.164 mmol) and sodium iodide (74 mg, 0.493 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (3 mL) followed by chlorotrimethylsilane (62 μL, 0.494 mmol) drop-wise. The reaction mixture is stirred at 60° C. under nitrogen for 12 hr. The reaction mixture is allowed to cool and then quenched with water (0.5 mL). After stirring for 30 min the mixture is diluted with water and extracted with five portions of dichloromethane. The combined dichloromethane layer is dried over magnesium sulfate and evaporated. The crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1, increasing to 19:1). Fractions containing the product are combined, the solvent evaporated and the residue triturated with heptane to give 3-ethyl-6-methyl-5-(1,2,4-oxadiazol-5-yl)-1H-pyridin-2-one (24 mg, 71% yield) as a white solid. LC/MS: RT: 2.37 min, MS: m/e=206 (M+H); 1H NMR (CDCl3, δ, ppm): 12.56 (1H, s), 8.44 (1H, s), 7.96 (1H, s), 2.82 (3H, s), 2.62 (2H, q), 1.26 (3H, t).

Provenance & Evidence