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

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posted on 2023-06-08, 19:53 authored by Mark BagleyMark Bagley, Jessica E Dwyer, Maria D Beltran Molina, Alexander W Rand, Hayley L Rand, Nicholas C O Tomkinson
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.

Funding

2012 Doctoral Training Grant (EPSRC); G0942; EPSRC-ENGINEERING & PHYSICAL SCIENCES RESEARCH COUNCIL; EP/K503198/1

Alignment of Synthesis, Medicinal Chemistry and Structural Genomics to Accelerate (Strathclyde lead); G0926; EPSRC-ENGINEERING & PHYSICAL SCIENCES RESEARCH COUNCIL; RKES 115428

History

Publication status

  • Published

File Version

  • Published version

Journal

Organic and Biomolecular Chemistry

ISSN

1477-0520

Publisher

Royal Society of Chemistry

Issue

24

Volume

13

Page range

6814-6824

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2015-06-15

First Open Access (FOA) Date

2015-06-15

First Compliant Deposit (FCD) Date

2015-06-15

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