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

doi:10.1016/j.tet.2007.08.069

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 journal › Article › peer-review

17 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 language	English (US)
Pages (from-to)	11763-11770
Number of pages	8
Journal	Tetrahedron
Volume	63
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2007.08.069
State	Published - Nov 19 2007
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.08.069

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

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.",

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

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T1 - A concise synthesis of quinazolinone TGF-β RI inhibitor through one-pot three-component Suzuki-Miyaura/etherification and imidate-amide rearrangement reactions

AU - Li, Hong yu

AU - Wang, Yan

AU - McMillen, William T.

AU - Chatterjee, Arindam

AU - Toth, John E.

AU - Mundla, Sreenivasa R.

AU - Voss, Matthew

AU - Boyer, Robert D.

AU - Sawyer, J. Scott

PY - 2007/11/19

Y1 - 2007/11/19

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AB - 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.

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

Abstract

ASJC Scopus subject areas

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