Concise, gram-scale synthesis of furo[2,3- b]pyridines with functional handles for chemoselective cross-coupling

Sean N O'Byrne; Benjamin J Eduful; Timothy M Willson; David H Drewry

doi:10.1016/j.tetlet.2020.152353

Concise, gram-scale synthesis of furo[2,3- b]pyridines with functional handles for chemoselective cross-coupling

Tetrahedron Lett. 2020 Sep 17;61(38):152353. doi: 10.1016/j.tetlet.2020.152353. Epub 2020 Aug 16.

Authors

Sean N O'Byrne¹, Benjamin J Eduful¹, Timothy M Willson¹, David H Drewry¹

Affiliation

¹ Structural Genomics Consortium, UNC Eshelman School of Pharmacy, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599, USA.

Abstract

A concise 4-step synthesis of furo[2,3-b]pyridines, with handles in the 3- and 5-positions for palladium mediated cross-coupling reactions, is described. The synthetic route has been optimized, with only one step requiring purification by column chromatography. The route is amenable to scale-up, and was successfully executed on a multi-gram scale. Furopyridines are of growing interest in medicinal chemistry, and this route should enable easy access to the core for structure-activity relationship (SAR) studies.

Keywords: Chemoselectivity; Furo[2,3-b]pyridines; Heterocycles; Hinge binders; Kinases.

Abstract

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