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

8 Citations (Scopus)

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.

LanguageEnglish
Pages6814-6824
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number24
DOIs
Publication statusPublished - 28 Jun 2015

Fingerprint

Thiophenes
Microwave irradiation
Microwaves
Dimethyl Sulfoxide
thiophenes
Scaffolds
inhibitors
Phosphotransferases
microwaves
preparation
synthesis
pyridines
irradiation
methyl thioglycolate
triethylamine
pyridine

Keywords

  • microwave irradiation
  • kinase inhibitors
  • PIM kinases

Cite this

Bagley, Mark C. ; Dwyer, Jessica E. ; Molina, Maria D Beltran ; Rand, Alexander W. ; Rand, Hayley L. ; Tomkinson, Nicholas C. O. / Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors. In: Organic and Biomolecular Chemistry. 2015 ; Vol. 13, No. 24. pp. 6814-6824.
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Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors. / Bagley, Mark C.; Dwyer, Jessica E.; Molina, Maria D Beltran; Rand, Alexander W.; Rand, Hayley L.; Tomkinson, Nicholas C. O.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 24, 28.06.2015, p. 6814-6824.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Microwave-assisted synthesis of 3-aminobenzo[b]thiophene scaffolds for the preparation of kinase inhibitors

AU - Bagley, Mark C.

AU - Dwyer, Jessica E.

AU - Molina, Maria D Beltran

AU - Rand, Alexander W.

AU - Rand, Hayley L.

AU - Tomkinson, Nicholas C. O.

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