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

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.

Iaroshenko V. O.; Wang Y.; Sevenard D. V.; Volochnyuk D. M.
Synthesis 2009, 11, 1851-1857
DOI: 10.1055/s-0029-1216640