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Paper | Regular issue | Vol 65, No. 9, 2005, pp.2071-2081
Published online, 2nd August, 2005
DOI: 10.3987/COM-05-10455
Nucleophilic Substitution Reaction of Amines with 3-Bromo-4-nitropyridine (and 2-Nitropyridine): A New Nitro-group Migration

Jiangchao Yao,* Paul R. Blake, and Ji Yang

*Computational, Combinatorial, and Medicinal Chemistry Department, Discovery Research, Purdue Pharma L.P., 6 Cedar Brook Drive, Cranbury, NJ 08512, U.S.A.

Abstract

On the reaction 3-bromo-4-nitropyridine with amine, three in stead of two expected products are separated. 2D NMR spectral data indicate the major product was an unexpected nitro-group migration product. To explore the rearrangement mechanism, a systematic study with various solvents and bases was undertaken. Results obtained indicate that nitro-group migration occurs in polar aprotic solvents; while expected nucleophilic substitution took place under all tested conditions.