Hydrochloric Acid → 2-{2-[3-(1H-imidazol-1-yl)phenyl]-2H-tetrazol-5-yl}pyridine

Participants

Reaction Conditions

Reaction Steps

2-[2-(3-Iodophenyl)-2H-tetrazol-5-yl]pyridine (520 mg, 1.5 mmol), imidazole (133 mg, 2.0 mmol), potassium carbonate (435 mg, 3.2 mmol), copper (I) iodide (57 mg, 0.3 mmol) and 1,2-diamino cyclohexane (90 μL, 0.8 mmol) were weighed into a flask and flushed with Ar(g). Dry dioxane (0.7 mL) was added and the reaction mixture heated at 100° C. for 18 h. The reaction mixture was then poured into NH4OH (10% in H2O), NH4Cl (sat aq) (1/1, 10 mL) and shaken with EtOAc (30 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (3×30 mL), the combined organics were dried over Na2SO4, filtered and concentrated onto silica gel. Purification by liquid chromatography on silica gel (hexane:EtOAc=90:10) gave a yellow solid. This was recrystallized from EtOAc/Hexane to give yellow crystals which were dissolved in CH2Cl2/Et2O and HCl in ether (1.5 equiv) was added. The resulting precipitate was filtered off to afford 2-{2-[3-(1H-imidazol-1-yl)phenyl]-2H-tetrazol-5-yl}pyridine as a yellow solid. 1H NMR ((CD3)2SO, 300 MHz) δ 9.94 (s, 1H), 8.23-8.84 (m, 1H), 8.68-8.69 (m, 1H), 8.48-8.49 (m, 1H), 8.39-8.42 (m, 1H), 8.30-8.33 (m, 1H) 8.07-8.13 (m, 2H), 7.97-8.03 (m, 2H), 7.63-7.67 (m, 1H). MS (ESI) 262.2 (MH-N2)+.

Provenance & Evidence