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Mohammed A Baashen

Leading speaker for catalysis conference 2017 - Mohammed A Baashen

Title: Microwave-Assisted Synthesis of a MK2 Inhibitor by Suzuki-Miyaura Coupling for Study in Werner Syndrome Cells using using a palladium catalyst

Mohammed A Baashen

Shaqra University, Saudi Arabia

Biography

Mohammed A Baashen is an Assistant Professor of Organic Chemistry at Shaqra University, College of Sciences and Humanities, Duwadmi, Saudi Arabia. He was educated as a Chemist at King Faisal University, Saudi Arabia (1995), and got his PhD from the University of Sussex with Professor Mark C Bagley (2013). His research involves the development of novel organic synthetic methods, especially using a relatively short reaction time to synthesised heterocyclic targets in high yield efficiently under microwave-assisted organic synthesis (MAOS) conditions and using Suzuki Coupling reactions for the development of a procedure for "palladium-catalyzed cross coupling," as an organic chemistry process, which enables the synthesis of large carbon-based molecules.

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.

Audience Takeaway:

•    Since its initial discovery as a Pd-catalyzed stereospecific cross-coupling reaction of 1-alkenylboranes, the Suzuki-Miyaura reaction has become one of the most efficient methods for C–C bond formation, in particular for aryl-aryl coupling. It offers many advantages over other methods, in that it is largely unaffected by the presence of water, produces non-toxic inorganic by-products that are easily removed, tolerates a broad range of functional groups and proceeds generally with regio- and stereocontrol. 

•    Werner syndrome (WS) is an example of a monogenic segmental progeroid syndrome—a rare human autosomal recessive genetic instability syndrome that mimics many, but not all, of the polygenic features of physiological aging. 

•    Suzuki-Miyaura cross-coupling reactions have been investigated for the synthesis of three different MK2 inhibitors for study in WS cells. 

•    This constitutes an extremely rapid method for access to this chemical tool, of value in elucidating the role of MK2 in accelerated aging in this progeroid syndrome.