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

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Bagley, Mark C. and Dwyer, Jessica E. and Molina, Maria D Beltran and Rand, Alexander W. and 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 (https://doi.org/10.1039/c5ob00819k)

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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.

ORCID iDs

Bagley, Mark C., Dwyer, Jessica E., Molina, Maria D Beltran ORCID logoORCID: https://orcid.org/0000-0001-8584-8956, Rand, Alexander W., Rand, Hayley L. and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
CORE (COnnecting REpositories)