Concise and efficient synthesis of 4-fluoro-1H-pyrrolo[2,3-b]pyridine

Carl Thibault; Alexandre L'Heureux; Rajeev S Bhide; Réjean Ruel

doi:10.1021/ol036030z

Concise and efficient synthesis of 4-fluoro-1H-pyrrolo[2,3-b]pyridine

Org Lett. 2003 Dec 25;5(26):5023-5. doi: 10.1021/ol036030z.

Authors

Carl Thibault¹, Alexandre L'Heureux, Rajeev S Bhide, Réjean Ruel

Affiliation

¹ Department of Discovery Chemistry, Pharmaceutical Research Institute, Bristol-Myers Squibb, 100 boulevard de l'Industrie, Candiac, Québec, Canada J5R 1J1.

PMID: 14682755
DOI: 10.1021/ol036030z

Abstract

Two routes describing the preparation of 4-fluoro-1H-pyrrolo[2,3-b]pyridine (4a) from 1H-pyrrolo[2,3-b]pyridine N-oxide (1) are presented. Regioselective fluorination was achieved using either the Balz-Schiemann reaction or lithium-halogen exchange. [reaction: see text]