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Microwave-Assisted Synthesis of a MK2 Inhibitor by Suzuki-Miyaura Coupling for Study in Werner Syndrome Cells

1
Department of Chemistry, School of Life Sciences, University of Sussex, Falmer, Brighton, East Sussex, BN1 9QJ, UK
2
Institute of Cancer and Genetics, Cardiff University School of Medicine, Heath Park, Cardiff, CF14 4XN, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Pharmaceuticals 2015, 8(2), 257-276; https://doi.org/10.3390/ph8020257
Received: 2 April 2015 / Revised: 13 May 2015 / Accepted: 1 June 2015 / Published: 3 June 2015
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. View Full-Text
Keywords: Suzuki-Miyaura; cross-coupling; MK2 inhibitor; Werner syndrome; cell aging; pyrazoles; heterocycles; microwave-assisted synthesis; boronic acid Suzuki-Miyaura; cross-coupling; MK2 inhibitor; Werner syndrome; cell aging; pyrazoles; heterocycles; microwave-assisted synthesis; boronic acid
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Bagley, M.C.; Baashen, M.; Chuckowree, I.; Dwyer, J.E.; Kipling, D.; Davis, T. Microwave-Assisted Synthesis of a MK2 Inhibitor by Suzuki-Miyaura Coupling for Study in Werner Syndrome Cells. Pharmaceuticals 2015, 8, 257-276.

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