Diethyl Ether → HCID 9812807, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence