Sodium Iodide → HCID 135438447, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl) pyridine (50 mg, 0.215 mmol) and sodium iodide (96 mg, 0.64 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (4 mL) followed by drop-wise chlorotrimethylsilane (82 μL, 0.653 mmol). The reaction mixture is stirred at 65° C. under nitrogen for 7 hr. The reaction mixture is allowed to cool and then quenched with water (0.5 mL). After stirring for 30 min the mixture 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 four further portions of dichloromethane. The combined organic 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). Fractions containing the product are combined and the solvent evaporated to give 3-ethyl-6-methyl-5-(3-methyl-1,2,4-oxadiazol-5-yl)-1H-pyridin-2-one (41 mg, 88% yield) as a white solid. LC/MS: RT: 2.44 min, MS: m/e=220 (M+H); 1H NMR (CDCl3, δ, ppm): 12.49 (1H, s), 7.92 (1H, s), 2.79 (3H, s), 2.61 (2H, q), 2.45 (3H, s), 1.25 (3H, t).

Provenance & Evidence