Water → 4-(5-{2-[2-(3-chloro-phenyl)-2H-tetrazol-5-yl]-vinyl}-4-ethyl-4H-[1,2,4]triazol-3-yl)pyridine

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Reaction Steps

4-Ethyl-5-pyridin-4-yl-4H-[1,2,4]triazole-3-carbaldehyde (56.4 mg, 0.279 mmol) was dissolved in dimethylformamide (2 mL) and added to a vial containing 2-(3-chloro-phenyl)-5-[(triphenyl-λ5-phosphanyl)-methyl]-2H-tetrazole hydrobromide (165.1 mg, 0.307 mmol) dissolved in dimethylformamide (2 mL). After addition of DBU (84.9 mg, 0.558 mmol), the vial was capped and the reaction was allowed to stir at room temperature for two hours. It was then heated at 80° C. for 1.5 hours. After cooling, water was added and an aqueous workup was done extracting with ethyl acetate three times. The combined organic layers were washed with water twice, brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by an SPE tube (5% MeOH/CH2Cl2) to yield the title compound as a white solid. 1H NMR (CDCl3) δ (ppm): 8.84 (d, 2H), 8.22 (m, 1H), 8.10 (d oft, 1H), 8.04 (d, 1H), 7.67 (d, 1H), 7.64 (m, 2H), 7.51 (m, 2H), 4.27 (q, 2H), 1.51 (t, 3H).

Provenance & Evidence