Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors

Bagley, Mark C, Dwyer, Jessica E, Beltran Molina, Maria D, Rand, Alexander W, Rand, Hayley L and Tomkinson, Nicholas C O (2015) Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors. Organic and Biomolecular Chemistry, 13 (24). pp. 6814-6824. ISSN 1477-0520

[img] PDF - Published Version
Available under License Creative Commons Attribution.

Download (486kB)

Abstract

Microwave irradiation of 2-halobenzonitriles and methyl thioglycolate in the presence of triethylamine in DMSO at 130 °C provides rapid access to 3-aminobenzo[b]thiophenes in 58–96% yield. This transformation has been applied in the synthesis of the thieno[2,3-b]pyridine core motif of LIMK1 inhibitors, the benzo[4,5]thieno[3,2-e][1,4]diazepin-5(2H)-one scaffold of MK2 inhibitors and a benzo[4,5]thieno[3,2-d]pyrimidin-4-one inhibitor of the PIM kinases.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Subjects: Q Science > QD Chemistry
Depositing User: Tom Gittoes
Date Deposited: 15 Jun 2015 13:05
Last Modified: 08 Mar 2017 12:55
URI: http://sro.sussex.ac.uk/id/eprint/52619

View download statistics for this item

📧 Request an update