introducing alkyne or azide into small molecule / click-chemistry - (Jan/29/2015 )

Dear all,

I would like to immobilize small molecules by click-chemistry for protein binding asays.

Does anyone of you have an idea how to introduce alkyne or azide groups into such a molecule (image attached)?

I tried the Mannich reaction on a DADPA resin, but the result wasn't satisfacory or at least hard to find very helpful.

Any help much appreciated

Well I am not a chemist and I think a chemist can give a better answer for this. But is it possible to introduce alkyl group on benzene ring using friedel-crafts alkylation. And then perform azidonation on that? 

Good idea. And the aniline is exactly the site I want to couple the compound. The only problem is though that the other ring systems would react too - and even more intensely - so the result would be an undesirable mixture of differently coupled molecules.