need solution for a synthetic problem

[sudhakar]

Hi everybody,

 

I am a new member to this forum and i want your help to get out of a synthetic problem with which i am strugling.

 

I am trying to prepare a organic compound in which i have started with 2,6 dibromo 4-nitro pyridine(self preparaed), one bromo to be suzuki coupled with azaindole and the other bromo buchwald to be done with benzyl amine and finally the nitro to be converted to fluoro which gives me desired compound.

 

Now the problem comes when all the couplings were done, the conversion of nitro to fluoro was failing.

 

I tried in the following methods TBAF/dmf,sandmeyer reaction,HBF4/NaNo2 but failed.

 

I also tried to fluorinate 2,6,dibromo 4- amino pyridine but it didn't work.

 

please help

Edited May 10, 2012 by sudhakar