[darkdevil]

Hi there,
Suppose I have the following compound:

I want to do nucleophilic aromatic substitution on the aromatic bromine group(s). I tried to do a typical Ullmann diary ether with a phenol (with K2CO3 as base and DMSO or DMF as solvent) and this compound, but it failed to give my product. (The reactant turned green which I suspect it is the anionic form of the N-H amine). It seems the N-H is quite reactive and it can act as a nucleophile and gave out side reactions.
I just wonder if there are any reaction conditions that can prevent this to occur? All I want to do is to either
1)add a vinyl polymerizing group to it or
2) do a main chain polymerization on this compound

[kriggy]

What about some protection of that amine?

[danny300]

good model...

[darkdevil]

What about some protection of that amine?

I don't want too much steps for this
I tried to do suzuki aryl-aryl coupling on the bromo position, but once again failed.
According to literatures, the indigo core is so electron deficient. May be this is the reason why many of the reactions do not proceed.
Can anyone give me some suggestions on how to "activate" this compound ?? Any help would be greatly appreciated!

[discodermolide]

As was said, you will probably have to protect the NH in order to do any meaningful chemistry with this compound.