The reaction of 4-nitro-3-bromopyridine (and 2-nitro-3-bromopyridine) with amine: A novel nitro-group migration

ORGN 153

Jiangchao Yao, jiangchao.yao@pharma.com, Ji Yang, ji.yang@pharma.com, and Paul Blake, paul.blake@pharma.com. Computational, Combinatorial, and Medicinal Chemistry Department, Purdue Pharma L.P, 6 Cedar Brook Drive, Cranbury, NJ 08512
In this poster, we will report our preliminary results on a novel nitro-group migration (rearrangement) on the pyridine ring. This work was initiated when we isolated an unexpected product 4 along with the expected products 3 and 5. The structures of 4 and 5 were characterized by LCMS, 1H NMR, 13C NMR and 2D NMR (NOE, HMBC, HMQC) spectra. The structure of compound 5 is further confirmed by an alternative synthetic route. The reaction between 6 and 2 also gives the similar results.

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005