The Journal of Organic Chemistry

Reaction of 3-substituted imidazo [1, 2-a] pyridines with bromine (1+) and the alleged 5-bromo-substituted product

ES Hand, WW Paudler

Index: Hand, E. Smakula; Paudler, William W. Journal of Organic Chemistry, 1980 , vol. 45, # 19 p. 3738 - 3745

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Abstract

The reaction of 3-methylimidazo [1, 2-a] pyridine with NBS was reinvestigated and is shown to give products formed by apparent nucleophilic substitution at the 2-position. NBS in CHCIB gave compounds 4 and 6, while NBS in CCl, or Br2 in CHC13 gave exclusively 4. Mechanisms and differences in product formation are discussed; evidence that the previously reported NBS product was in fact 3-bromo-5-methylimidazo [ 1, 2-a] pyridine, ...