Hydrochloric Acid → HCID 69093424, compound

Participants

Reaction Steps

To a solution of 1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-5-carbonitrile (I-33, 120 mg, 0.430 mmol) in methanol (2.0 mL) was added cesium carbonate (280 mg, 0.859 mmol). After stirring at room temperature for 3.75 h, aqueous 0.1 N hydrochloric acid (10 mL) was added, followed by aqueous 1 N hydrochloric acid (˜1 mL) until pH ˜3. After stirring for 45 min, the methanol was removed in vacuo, and the crude residue was brought up in ethyl acetate (75 mL) and saturated aqueous sodium bicarbonate (50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (2×50 mL). The organics were washed with brine (50 mL), dried over magnesium sulfate, filtered, and the solvent was removed in vacuo to give the crude product as white solid. Purification by silica gel chromatography (20-80% ethyl acetate in hexanes) gave methyl 1-(2-fluorobenzyl)-3-(pyridin-2-yl)-1H-1,2,4-triazole-5-carboxylate (99% yield) as a white solid.

Provenance & Evidence