A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid

Xin Wang, Ben Zhi, Jean Baum, Ying Chen, Richard Crockett, Liang Huang, Shawn Eisenberg, John Ng, Robert Larsen, Mike Martinelli, Paul Reider

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Abstract

A practical synthesis of a key pharmaceutical intermediate, 2-[(1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino]-5-fluoronicotinic acid (1), is described. To introduce the aminomethyl moiety of 2 via a palladium-catalyzed cyanation/reduction sequence, a regioselective chlorination of 7-azaindole via the N-oxide was developed. A highly selective monodechlorination of 2,6-dichloro-5-fluoronicotinic acid was discovered to afford the nicotinic acid 3. The two building blocks 2 and 3 were then coupled to complete the preparation of 1.

Original languageEnglish (US)
Pages (from-to)4021-4023
Number of pages3
JournalJournal of Organic Chemistry
Volume71
Issue number10
DOIs
StatePublished - May 12 2006
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Wang, X., Zhi, B., Baum, J., Chen, Y., Crockett, R., Huang, L., Eisenberg, S., Ng, J., Larsen, R., Martinelli, M., & Reider, P. (2006). A practical synthesis of 2-((1H-pyrrolo[2,3-b]pyridine-4-yl)methylamino)-5- fluoronicotinic acid. Journal of Organic Chemistry, 71(10), 4021-4023. https://doi.org/10.1021/jo0602571