Sodium Iodide → HCID 135513085, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(1,2,4-oxadiazol-3-yl)pyridine (56 mg, 0.256 mmol) and sodium iodide (117 mg, 0.78 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (4 mL) followed by drop-wise addition of chlorotrimethylsilane (97.5 μL, 0.776 mmol). The reaction mixture is stirred at 65° C. under nitrogen for 16 hr. The reaction mixture is allowed to cool, diluted with water and the resulting mixture is extracted with five portions of dichloromethane. The combined extract is dried over magnesium sulfate and evaporated to leave a brown residue. This material is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (49:1). Fractions containing the product are combined and the solvent evaporated, to give 3-ethyl-6-methyl-5-(1,2,4-oxadiazol-3-yl)-1H-pyridin-2-one (38 mg, 73% yield) as a off-white solid. LC/MS: RT: 2.27 min, m/e=206 (M+H); 1H NMR (400 MHz, δ, ppm): 12.02 (1H, s), 9.64 (1H, s), 7.74 (1H, s), 2.52 (3H, s), 2.41 (2H, q), 1.10 (3H, t).

Provenance & Evidence