Potassium Carbonate → 2-[1-(3-Chlorophenyl)-1H-1,2,4-triazol-3-yl]pyridine

Temperature

100 °C

2-(1H-1,2,4-Triazol-3-yl)pyridine (1.0 g, 6.8 mmol), potassium carbonate (1.88 g, 13.6 mmol) and 1-chloro-3-fluorobenzene (0.89 g, 6.8 mmol) were stirred in DMF (20 mL) at ambient temperature. The resulting reaction mixture was heated at 100° C. for 16 h, after which time it was quenched with H2O (50 mL) and diluted with EtOAc (200 mL). The EtOAc solution was washed with H2O (3×100 mL), then brine (100 mL) and dried (MgSO4), filtered and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with hexanes: EtOAc (40:60) to afford 2-[1-(3-chlorophenyl)-1H-1,2,4-triazol-3-yl]pyridine as a white solid which was then dissolved in dichloromethane (5 mL) and precipitated as the hydrochloride salt (M.p.=221–223° C.) upon treatment with 1M HCl in diethyl ether (5 mL).

1. customThe resulting reaction mixture
2. customafter which time it was quenched with H2O (50 mL)
3. additiondiluted with EtOAc (200 mL)
4. washThe EtOAc solution was washed with H2O (3×100 mL)
5. dry with materialbrine (100 mL) and dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was chromatographed on silica gel
9. washeluting with hexanes: EtOAc (40:60)

ORD record

ord-22339c1b989e47cc91c838e2af7f22bc

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105548B2