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 Citations (Scopus)

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
Externally publishedYes

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Imidoesters
Quinazolinones
Boronic Acids
Microwaves
Amides
Heating
Temperature
Microwave heating
Purification
methanesulfonyl chloride

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A concise synthesis of quinazolinone TGF-β RI inhibitor through one-pot three-component Suzuki-Miyaura/etherification and imidate-amide rearrangement reactions. / Li, Hong Yu; Wang, Yan; McMillen, William T.; Chatterjee, Arindam; Toth, John E.; Mundla, Sreenivasa R.; Voss, Matthew; Boyer, Robert D.; Sawyer, J. Scott.

In: Tetrahedron, Vol. 63, No. 47, 19.11.2007, p. 11763-11770.

Research output: Contribution to journalArticle

Li, Hong Yu ; Wang, Yan ; McMillen, William T. ; Chatterjee, Arindam ; Toth, John E. ; Mundla, Sreenivasa R. ; Voss, Matthew ; Boyer, Robert D. ; Sawyer, J. Scott. / A concise synthesis of quinazolinone TGF-β RI inhibitor through one-pot three-component Suzuki-Miyaura/etherification and imidate-amide rearrangement reactions. In: Tetrahedron. 2007 ; Vol. 63, No. 47. pp. 11763-11770.
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