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

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.

SUBMITTER: O'Byrne SN

PROVIDER: S-EPMC7526865 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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

O'Byrne Sean N SN Eduful Benjamin J BJ Willson Timothy M TM Drewry David H DH

Tetrahedron letters 20200816 38

A concise 4-step synthesis of furo[2,3-<i>b</i>]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 relat ...[more]

PMID: 33012852

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