Sodium Iodide → HCID 135509914, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-ethyl-2-methoxy-6-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-pyridine (47 mg, 0.202 mmol) and sodium iodide (91 mg, 0.607 mmol) under a nitrogen atmosphere is added anhydrous acetonitrile (4 mL) followed by drop-wise addition of chlorotrimethylsilane (76 μL, 0.605 mmol). The reaction mixture is stirred at 65° C. under nitrogen for 15 hr. The reaction mixture is allowed to cool, diluted with water and the resulting mixture is extracted with four portions of dichloromethane. The combined extracts are dried over magnesium sulfate and evaporated to leave an orange residue. The crude product is purified by flash chromatography on a 2-gram silica gel cartridge by elution with heptane:dichloromethane: (1:1). Fractions containing the product are combined, the solvent evaporated and the residue triturated with ether to 3-ethyl-6-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)-1H-pyridin-2-one (25 mg, 58% yield) as a light yellow powder. LC/MS: RT: 2.39 min, MS: m/e=220 (M+H); 1H NMR (CDCl3, δ, ppm): 12.14 (1H, s), 7.89 (1H, s), 2.70 (3H, s), 2.64 (3H, s), 2.61 (2H, q), 1.24 (3H, t).

Provenance & Evidence