Sodium Iodide → HCID 135530195, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(5-methyl-[1,3,4]oxadiazol-2-yl)pyridine (95 mg, 0.408 mmol) and sodium iodide (182 mg, 1.21 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (3 mL) followed by chlorotrimethylsilane (156 μL, 1.24 mmol). The reaction mixture is stirred at 50° C. under nitrogen for 2.5 hr. The reaction mixture is allowed to cool and then quenched with water (0.5 mL). After stirring for 30 min the mixture is evaporated. The residue is partitioned between water and dichloromethane and the mixture treated with a little sodium bisulfite to decolorize. The dichloromethane layer is separated and the aqueous layer is extracted with five portions of dichloromethane. The combined dichloromethane layer is washed with two portions of aqueous sodium hydroxide (1M), then dried over magnesium sulfate and evaporated to give an orange residue. The crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:methanol (30:1). The clean fractions containing the product are combined and evaporated to give 3-ethyl-6-methyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyridin-2-one (38 mg, 43% yield) as a white solid. LC/MS: RT: 2.10 min, MS: m/e=220 (M+H); 1H NMR (300 MHz, CDCl3, δ, ppm): 12.24 (1H, s), 7.76 (1H, s), 2.76 (3H, s), 2.61 (2H, q), 2.61 (3H, s), 1.25 (3H, t).

Provenance & Evidence