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Synthesis 1996; 1996(7): 877-882
DOI: 10.1055/s-1996-4312
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A Convenient Method for the Preparation of 5-, 6- and 7-Azaindoles and Their Derivatives

David Hands* , Brian Bishop, Mark Cameron, John S. Edwards, Ian F. Cottrell, Stanley H. B. Wright
  • *Merck Sharp and Dohme Research Laboratories, Hertford Road, Hoddesdon, Hertfordshire, EN11 9BU, England, Fax +44(1992)470437
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Publication Date:
31 December 2000 (online)

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The directed ortho lithiation of 2-tert-butoxycarbonylamino-3-methylpyridine (6a) has provided a convenient method for the preparation of 1H-pyrrolo[2,3-b]pyridine (4a, 7-azaindole). This procedure has been used to prepare a range of 3-substituted 2-tert-butoxycarbonylaminopyridines 6, 2- and 3-substituted and 2,3-disubstituted 1H-pyrrolo[2,3-b]pyridines 4 and shown to be of value in the preparation of 1H-pyrrolo[3,2-c]pyridine (15, 5-azaindole) and 1H-pyrrolo[2,3-c]pyridine (18, 6-azaindole) and derivatives.

directed ortho metallation - 3-substituted-2-aminopyridines - 5,- 6- and 7-azaindoles