Triazolopyridines are an important class of heterocyclic compounds in medicinal chemistry and the materials industry. (1−3) Among these, [1,2,3]triazolo[1,5a]pyridines have emerged as antiparasitic agents for Chagas disease treatment, (4,5) and stable carbene precursors for accessing pyridyl diazo intermediates through ring–chain isomerization in chemocatalysis, (1,6) and biocatalysis (Figure 1a).