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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 |

REPOSITORIES: biostudies-literature

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Structure-activity relationships in human Toll-like receptor 8-active 2,3-diamino-furo[2,3-c]pyridines.

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4,8-Dimeth-oxy-furo[2,3-b]quinoline (?-fagarine).

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3,3-Ethyl-enedithio-3,3a,4,5,10,10b-hexa-hydro-2H-furo[2,3-a]carbazole.

Project description:The title compound, C(16)H(17)NOS(2), consists of a carbazole skeleton with tetra-hydro-furan and dithiol-ane rings. In the indole ring system, the benzene and pyrrole rings are nearly coplanar, forming a dihedral angle of 1.57?(15)°. The cyclo-hexenone and tetra-hydro-furan rings have envelope conformations, while the dithiol-ane ring adopts a twist conformation. In the crystal structure, pairs of weak inter-molecular N-H?S hydrogen bonds link the mol-ecules into centrosymmetric dimers with R(2) (2)(16) ring motifs. Weak C-H?? inter-actions may further stabilize the structure.

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