Title:
METHOD FOR FORMING BOND THROUGH COUPLING REACTION
Document Type and Number:
WIPO Patent Application WO/2023/054715
Kind Code:
A1
Abstract:
The present invention provides a method for producing a compound through a cross-coupling reaction, wherein: the method for producing a compound includes reacting a compound 1 having a leaving group X1 on a carbon atom of an aromatic ring, and a compound 2 having a reactive group capable of a C-O bond-forming reaction or a C-N bond-forming reaction through substitution with the aforementioned leaving group, in a solvent that includes an amide solvent represented by formula A [in the formula, R1, R2, and R3 each independently represent a C1-4 alkyl, where the total number of carbon atoms in R1, R2, and R3 is 4-6] in the presence of a catalyst and a base; and X1 is a halogen atom or -O-SO2-R4.
Inventors:
ITO TAISUKE (JP)
Application Number:
PCT/JP2022/036853
Publication Date:
April 06, 2023
Filing Date:
September 30, 2022
Export Citation:
Assignee:
CHUGAI PHARMACEUTICAL CO LTD (JP)
International Classes:
C07D211/46; C07B61/00; C07D401/12; C07D401/14; C07D409/14; C07D417/14; C40B50/14
Foreign References:
| US4453017A | 1984-06-05 | |||
| JP2006213692A | 2006-08-17 |
Other References:
WOLFE J P, BUCHWALD S L: "Nickel-Catalyzed Amination of Aryl Chlorides", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 119, no. 26, 1 January 1997 (1997-01-01), pages 6054 - 6058, XP002442784, ISSN: 0002-7863, DOI: 10.1021/ja964391m
BING ZHENG; TIEZHENG JIA; PATRICK J. WALSH: "A General and Practical Palladium‐Catalyzed Direct α‐Arylation of Amides with Aryl Halides", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 356, no. 1, 10 January 2014 (2014-01-10), Hoboken, USA, pages 165 - 178, XP072353523, ISSN: 1615-4150, DOI: 10.1002/adsc.201300851
TAKUO HAMA, DARCY A. CULKIN, JOHN F. HARTWIG: "Palladium-Catalyzed Intermolecular α-Arylation of Zinc Amide Enolates under Mild Conditions", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 128, no. 15, 1 April 2006 (2006-04-01), pages 4976 - 4985, XP055095770, ISSN: 0002-7863, DOI: 10.1021/ja056076i
DOREL, R ET AL., ANGEW. CHEM. INT. ED., vol. 58, 2019, pages 17118
SURRY, D.S. ET AL., CHEM. SCI, 27 February 2011 (2011-02-27)
ANDERSON, K.W. ET AL., J. AM. CHEM. SOC., vol. 128, 2006, pages 10694
SHERWOOD, J. ET AL., GREEN. CHEM, vol. 21, 2019, pages 2164
MOLINA DE LA TORRE, J.A ET AL., ORGANOMETALLICS, vol. 32, 2013, pages 5428 - 5434
SANTANILLA, A.B. ET AL., ORGANIC LETTERS, vol. 17, 2015, pages 3370 - 3373
YANG, J.C. ET AL., ANGEW. CHEM. INT. ED, vol. 55, 2016, pages 2531
ANGEW. CHEM. INT. ED., vol. 55, 2016, pages 2531 - 2535
BING ZHENG; TIEZHENG JIA; PATRICK J. WALSH: "A General and Practical Palladium‐Catalyzed Direct α‐Arylation of Amides with Aryl Halides", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 356, no. 1, 10 January 2014 (2014-01-10), Hoboken, USA, pages 165 - 178, XP072353523, ISSN: 1615-4150, DOI: 10.1002/adsc.201300851
TAKUO HAMA, DARCY A. CULKIN, JOHN F. HARTWIG: "Palladium-Catalyzed Intermolecular α-Arylation of Zinc Amide Enolates under Mild Conditions", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 128, no. 15, 1 April 2006 (2006-04-01), pages 4976 - 4985, XP055095770, ISSN: 0002-7863, DOI: 10.1021/ja056076i
DOREL, R ET AL., ANGEW. CHEM. INT. ED., vol. 58, 2019, pages 17118
SURRY, D.S. ET AL., CHEM. SCI, 27 February 2011 (2011-02-27)
ANDERSON, K.W. ET AL., J. AM. CHEM. SOC., vol. 128, 2006, pages 10694
SHERWOOD, J. ET AL., GREEN. CHEM, vol. 21, 2019, pages 2164
MOLINA DE LA TORRE, J.A ET AL., ORGANOMETALLICS, vol. 32, 2013, pages 5428 - 5434
SANTANILLA, A.B. ET AL., ORGANIC LETTERS, vol. 17, 2015, pages 3370 - 3373
YANG, J.C. ET AL., ANGEW. CHEM. INT. ED, vol. 55, 2016, pages 2531
ANGEW. CHEM. INT. ED., vol. 55, 2016, pages 2531 - 2535
Attorney, Agent or Firm:
YAMAMOTO, Osamu et al. (JP)
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