[Aerosolid]

Hi! I am wondering if anyone knows why the site of triflation changes when this rxn is run in another solvent. (see the attached file for the rxn equation) .

[wildfyr]

I note that the solvent isn't the only difference. What are your first thoughts? Here we only help those who demonstrate that they have put effort into solving problems themselves.

[Aerosolid]

Yea, well, in the rxn where the pyridone oxygen is tosylated a DTBMP base is applied. I imagine that the base might thoroughly deprotonate the pyridine nitrogen, thus adding a formal negative which would be delocalized onto to the oxygen. But would this make the oxygen more nucleophilic than the nitrogen?

[wildfyr]

I think a phenolate is more nucleophilic than an aniline.