Diethyl Ether → HCID 9812807, compound

Temperature

95 °C

2-Ethynylpyridine (3.1 g, 30 mmol) and trimethylsilylazide (7.9 mL, 60 mmol) were combined under Ar (g) and heated at 95° C. for 18 h. After cooling to ambient temperature, Et2O (50 mL) and H2O (2 mL) were added and the resulting reaction mixture was stirred for 2 h. The reaction mixture was then extracted with H2O (3×50 mL) and the organic layer extracted with 1M KOH (3×30 mL). The two aqueous layers were combined and the pH adjusted to 7 with HCl (2M), extracted with EtOAc (3×50 mL), dried over Na2SO4 and concentrated in vacuo to afford 2-(2H-1,2,3-triazol-4-yl)pyridine as a brown solid that was used without further purification.

1. temperatureAfter cooling to ambient temperature
2. customthe resulting reaction mixture
3. extractionThe reaction mixture was then extracted with H2O (3×50 mL)
4. extractionthe organic layer extracted with 1M KOH (3×30 mL)
5. extractionextracted with EtOAc (3×50 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-b3b14cbc40574018ba891e988eb6bdab

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07105548B2