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

Mark C. Bagley, Jessica E. Dwyer, Maria D Beltran Molina, Alexander W. Rand, Hayley L. Rand, Nicholas C. O. Tomkinson

Research output: Contribution to journalArticle

13 Citations (Scopus)
119 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)6814-6824
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number24
DOIs
Publication statusPublished - 28 Jun 2015

Keywords

  • microwave irradiation
  • kinase inhibitors
  • PIM kinases

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