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Microwave-assisted Ullmann C-S bond formation: synthesis of the P38 alpha MAPK clinical candidate VX-745

Bagley, Mark Christopher, Davis, Terence, Dix, Matthew Charles, Fusillo, Vincenzo, Pigeaux, Morgane, Rokicki, Michal Jaroslaw and Kipling, David Glyn 2009. Microwave-assisted Ullmann C-S bond formation: synthesis of the P38 alpha MAPK clinical candidate VX-745. Journal of Organic Chemistry 74 (21) , pp. 8336-8342. 10.1021/jo9017155

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Abstract

Microwave irradiation promotes the rapid and efficient reaction of a thiophenol and aryl or heteroaryl halide using a copper or palladium catalyst and a range of ligands, depending upon substrate. Of particular utility is the use of copper(I) iodide (5 mol and trans-cyclohexane-1,2-diol as ligand under basic conditions and microwave irradiation to give the corresponding sulfide in high yield. This method for C-S bond formation is applied in the four-step synthesis of the clinical candidate VX-745 in 38% overall yield. The inhibitory activity of VX-745 against p38alpha MAPK is confirmed in Werner syndrome dermal fibroblasts at 1.0 microM concentration by immunoblot assay.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: American Chemical Society
ISSN: 0022-3263
Last Modified: 06 Feb 2020 21:47
URI: http://orca.cf.ac.uk/id/eprint/23857

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