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Microwave-assisted synthesis of a MK2 inhibitor by Suzuki-Miyaura coupling for study in Werner Syndrome Cells

Bagley, Mark, Baashen, Mohammed, Chuckowree, Irina, Dwyer, Jessica, Kipling, David Glyn and Davis, Terence 2015. Microwave-assisted synthesis of a MK2 inhibitor by Suzuki-Miyaura coupling for study in Werner Syndrome Cells. Pharmaceuticals 8 (2) , pp. 257-276. 10.3390/ph8020257

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Abstract

Microwave-assisted Suzuki-Miyaura cross-coupling reactions have been employed towards the synthesis of three different MAPKAPK2 (MK2) inhibitors to study accelerated aging in Werner syndrome (WS) cells, including the cross-coupling of a 2-chloroquinoline with a 3-pyridinylboronic acid, the coupling of an aryl bromide with an indolylboronic acid and the reaction of a 3-amino-4-bromopyrazole with 4-carbamoylphenylboronic acid. In all of these processes, the Suzuki-Miyaura reaction was fast and relatively efficient using a palladium catalyst under microwave irradiation. The process was incorporated into a rapid 3-step microwave-assisted method for the synthesis of a MK2 inhibitor involving 3-aminopyrazole formation, pyrazole C-4 bromination using N-bromosuccinimide (NBS), and Suzuki-Miyaura cross-coupling of the pyrazolyl bromide with 4-carbamoylphenylboronic acid to give the target 4-arylpyrazole in 35% overall yield, suitable for study in WS cells.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Medicine
Subjects: R Medicine > R Medicine (General)
Publisher: MDPI AG
ISSN: 1424-8247
Date of First Compliant Deposit: 30 March 2016
Date of Acceptance: 1 June 2015
Last Modified: 10 Jun 2019 10:50
URI: http://orca-mwe.cf.ac.uk/id/eprint/83159

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