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

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.

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: [phone];
e-mail: [e-mail].