A concise synthesis of quinazolinone TGF-β RI inhibitor through one-pot three-component Suzuki-Miyaura/etherification and imidate-amide rearrangement reactions

Hong yu Li, Yan Wang, William T. McMillen, Arindam Chatterjee, John E. Toth, Sreenivasa R. Mundla, Matthew Voss, Robert D. Boyer, J. Scott Sawyer

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

A simple and efficient synthesis of dihydropyrrolopyrazole boronic acid intermediate (5) has been developed. Utilization of a three-component Suzuki-Miyaura/etherification with microwave heating led to advanced compound 11 in high yield and with easy purification. Reaction of compound 11 with methanesulfonyl chloride at room temperature furnished the 1,3 O-N rearranged product (12), which is postulated to proceed via an intramolecular mechanism. The outlined synthesis provides a highly efficient and high-yielding route that is amenable to rapid analog synthesis.

Original languageEnglish (US)
Pages (from-to)11763-11770
Number of pages8
JournalTetrahedron
Volume63
Issue number47
DOIs
StatePublished - Nov 19 2007

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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