Potassium Carbonate → HCID 11708269, compound

Participants

Reaction Conditions

Reaction Steps

Into a microwave vial is added 3-bromo-5-ethyl-6-methoxy-2-methyl-pyridine (400 mg, 1.74 mmol), potassium carbonate (360 mg, 2.61 mmol), copper iodide (50 mg, 0.263 mmol) and 1,2,3-triazole (201 μL, 3.47 mmol). The vial is flushed with nitrogen before anhydrous dimethylformamide (4 mL) is added then sealed. The reaction is heated in the CEM Discover microwave at 185° C. for 20 min (4 bar pressure attained). LC/MS shows the reaction is incomplete. The reaction is re-microwaved to 180° C. for 20 min. Further copper iodide (50 mg) is added, the reaction flushed with nitrogen and is re-microwaved to 180° C. for 20 min. LC/MS shows the reaction is complete with the formation of 2 materials. The reaction is diluted with water and extracted with six portions of dichloromethane. The combined extracts are then dried over magnesium sulfate and evaporated to give a dark oil. The crude product is purified by flash chromatography on a 5-gram silica gel cartridge by elution with dichloromethane:ethyl acetate (3:1, increasing to 2:1 then 1:1). Fractions containing the higher Rf product are combined, the solvent evaporated and the residue is triturated twice with heptane and twice with ether to give 3-ethyl-6-methyl-5-(1,2,3-triazol-2-yl)-1H-pyridin-2-one (40 mg, 11% yield) as a white powder. LC/MS: RT: 2.19 min, MS: m/e=205 (M+H); 1H NMR (δ, ppm): 11.93 (1H, s), 8.04 (2H, s), 7.40 (1H, s), 2.41 (2H, q), 2.06 (3H, s), 1.09 (3H, t).

Provenance & Evidence