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Synthesis 2009(11): 1851-1857  
DOI: 10.1055/s-0029-1216640
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Fluorinated Pyrrolo[2,3-b]pyridine and Pyrrolo[2,3-d]pyrimidine Nucleosides

Viktor O. Iaroshenko*a,b, Yan Wangc, Dmitri V. Sevenardd, Dmitriy M. Volochnyuka,e
a Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kyiv-33, Ukraine
c Fachbereich Chemie, Universität Konstanz, Fach M-720, Universitätsstr.10, 78457 Konstanz, Germany
d Hansa Fine Chemicals GmbH, BITZ, Fahrenheitstrasse 1, 28359 Bremen, Germany
e Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kyiv-94, Ukraine
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Publication History

Received 24 October 2008
Publication Date:
12 May 2009 (online)

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Abstract

With the purpose of synthesizing novel ADAs (adenosine deaminase) and IMPDH (inosine 5′-monophosphate dehydrogenase) inhibitors the reactions of 5-amino-1-tert-butyl-1-H-pyrrole-3-carbonitrile with fluorinated 1,3- -bielectrophiles were studied. An efficient and convenient synthetical approach to fluorinated pyrrolo[2,3-b]pyridines was developed. The tert-butyl protecting group was successfully removed by treating the pyrrolopyridines or -pyrimidines with 60% sulfuric acid and this was followed by direct glycosylation of the products.

Key words

pyrrole - amine - fluorine - pyridine - annulation - electrophilic aromatic substitution

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Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 703680 and CCDC 683574 can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033;
e-mail: deposit@ccdc.cam.ac.uk.