Concise, gram-scale synthesis of furo2,3-bpyridines with functional handles for chemoselective cross-coupling

• Published in: Tetrahedron letters 2020-09, Vol.61 (38)
• Main Authors: O'Byrne, Sean N, Eduful, Benjamin J, Willson, Timothy M, Drewry, David H
• Format: Article
• Language: English
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2020.152353

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.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.