[UnderGrad]

I want to do a nucleophilic substitution with 4-hydroxypyridine. I want to form the cooresponding  sodium salt at the alchohol functionality (O-) and need to protect the nitrogen somehow. I don't know if a BOC or Tosyl group can be used because it's not an amine. Then I need to deprotect the N, and bind the N to a transition metal (use the molecule as a ligand to secure the metal). I won't lie... I'm not even sure this is feasable.

Any suggestions?

[Doc Oc]

What do you plan on doing with the sodium salt of the hydroxy anion before attaching the pyridine to the metal center?

There are ways to temporarily protect a pyridine nitrogen, but they can be tricky and doing any further chemistry on the molecule is not straight forward due to the change in reactivity (ie; working with a pyridinium rather than pyridine).

[UnderGrad]

So I want to attach the oxygen to a polymer and then attach an active catalyst to the nitrogen. A polymer supported catalyst system. It's a little complicated to explain in full detail. Basicly I need to protect the nitrogen attach the ligand to the polymer, deprotect the nitrogen so it can coordinate to the metal center. I see some protecting groups based on the pyridimium ion but then can I even form the oxy salt? Plus I need this reaction to go down in organic solvent and that seems like a lot of ionic character. I really don't know how to approach the synthesis. The polymer is soluble in THF and dioxanes. Maybe DMF or DMSO. I'd need obviously need basic conditions to form the oxy salt. If i used say, borane to protect the nitrogen, and then introduced the molecule in basic conditions (NaH) would the hyrdide displace the borane?