Title:
METHOD OF PRODUCING 3-METHYL-4-HALO-INDOLE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2022/092247
Kind Code:
A1
Abstract:
The present inventors found a novel method of reducing a formyl group with the use of a Lewis acid and a hydride reducing agent in a production process of a 3-methyl-4-halo-indole derivative. Further, the present inventors found that demethylation and/or dehalogenation of the aforesaid derivative are suppressed by this method so that a posttreatment can be facilitated or the derivative can be obtained at a high yield.
Inventors:
SAKURAI NATSUKI (JP)
SAKAMOTO TATSUHIRO (JP)
OGURA TOMOKAZU (JP)
SAKAMOTO TATSUHIRO (JP)
OGURA TOMOKAZU (JP)
Application Number:
PCT/JP2021/039946
Publication Date:
May 05, 2022
Filing Date:
October 29, 2021
Export Citation:
Assignee:
DAIICHI SANKYO CO LTD (JP)
International Classes:
C07D209/08; A61K31/422; A61P35/00; B01J31/24; C07B61/00; C07D413/06
Domestic Patent References:
| WO2016052697A1 | 2016-04-07 | |||
| WO2016052697A1 | 2016-04-07 |
Foreign References:
| CN104230781A | 2014-12-24 | |||
| CN106565683A | 2017-04-19 | |||
| JP2009541461A | 2009-11-26 | |||
| JP2014521607A | 2014-08-28 | |||
| JP2014524456A | 2014-09-22 | |||
| JP2019131672A | 2019-08-08 | |||
| JP2019094299A | 2019-06-20 |
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CHEN WEILIANG, XIA YONG, LIN LILI, YUAN XIAO, GUO SONGSONG, LIU XIAOHUA, FENG XIAOMING: "Asymmetric Synthesis of Furo[3,4- b ]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 21, no. 43, 19 October 2015 (2015-10-19), DE, pages 15104 - 15107, XP055926507, ISSN: 0947-6539, DOI: 10.1002/chem.201502448
SHOHJI NORIAKI, KAWAJI TSUYOSHI, OKAMOTO SENTARO: "Ti(O- i -Pr) 4 /Me 3 SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 10, 20 May 2011 (2011-05-20), US , pages 2626 - 2629, XP055926512, ISSN: 1523-7060, DOI: 10.1021/ol200740r
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NAKAGAWA MAKOTO; NAKATANI FUMIHIKO; MATSUNAGA HIRONORI; SEKI TAKAHIKO; ENDO MAKOTO; OGAWARA YOKO; MACHIDA YUKINO; KATSUMOTO TAKUO;: "Selective inhibition of mutant IDH1 by DS-1001b ameliorates aberrant histone modifications and impairs tumor activity in chondrosarcoma", ONCOGENE, NATURE PUBLISHING GROUP UK, LONDON, vol. 38, no. 42, 12 August 2019 (2019-08-12), London , pages 6835 - 6849, XP036906411, ISSN: 0950-9232, DOI: 10.1038/s41388-019-0929-9
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T. W. GREENP.G.M. WUTS: "Protective Groups in Organic Synthesis", 2006, JOHN WILEY & SONS, INC.
BAI JIAN-FEI, ZHAO LULU, WANG FANG, YAN FACHAO, KANO TAICHI, MARUOKA KEIJI, LI YUEHUI: "Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2- a ]indoles via Dynamic Kinetic Resolution of Allene Intermediates", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 22, no. 14, 17 July 2020 (2020-07-17), US , pages 5439 - 5445, XP055926497, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.0c01812
WANG SHUAI, SHEN YAO-BIN, LI LONG-FEI, QIU BIN, YU LIPING, LIU QING, XIAO JIAN: "N -Alkylation-Initiated Redox-Neutral [5 + 2] Annulation of 3-Alkylindoles with o -Aminobenzaldehydes: Access to Indole-1,2-Fused 1,4-Benzodiazepines", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 21, no. 22, 15 November 2019 (2019-11-15), US , pages 8904 - 8908, XP055926500, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.9b03011
DUAN SHENGGUO, AN YUEHUI, XUE BING, CHEN YIDIAN, ZHANG WAN, XU ZE‐FENG, LI CHUAN‐YING: "Synthesis of Pyrido[2,3‐ b ]indole Derivatives via Rhodium‐Catalyzed Cyclization of Indoles and 1‐Sulfonyl‐1,2,3‐triazoles", ADVANCED SYNTHESIS AND CATALYSIS, vol. 362, no. 9, 27 April 2020 (2020-04-27), pages 1831 - 1835, XP055926504, ISSN: 1615-4150, DOI: 10.1002/adsc.201901599
CHEN WEILIANG, XIA YONG, LIN LILI, YUAN XIAO, GUO SONGSONG, LIU XIAOHUA, FENG XIAOMING: "Asymmetric Synthesis of Furo[3,4- b ]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides", CHEMISTRY - A EUROPEAN JOURNAL, JOHN WILEY & SONS, INC, DE, vol. 21, no. 43, 19 October 2015 (2015-10-19), DE, pages 15104 - 15107, XP055926507, ISSN: 0947-6539, DOI: 10.1002/chem.201502448
SHOHJI NORIAKI, KAWAJI TSUYOSHI, OKAMOTO SENTARO: "Ti(O- i -Pr) 4 /Me 3 SiCl/Mg-Mediated Reductive Cleavage of Sulfonamides and Sulfonates to Amines and Alcohols", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 13, no. 10, 20 May 2011 (2011-05-20), US , pages 2626 - 2629, XP055926512, ISSN: 1523-7060, DOI: 10.1021/ol200740r
HARADA, K. URABE, H. SATO, F.: "Generation and Reactions of Low-Valent Titanium Alkoxide-Acetylene Complexes. A Practical Preparation of Allyl Alcohols", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 36, no. 18, 1 May 1995 (1995-05-01), Amsterdam , NL , pages 3203 - 3206, XP004028226, ISSN: 0040-4039, DOI: 10.1016/0040-4039(95)00513-C
NAKAGAWA MAKOTO; NAKATANI FUMIHIKO; MATSUNAGA HIRONORI; SEKI TAKAHIKO; ENDO MAKOTO; OGAWARA YOKO; MACHIDA YUKINO; KATSUMOTO TAKUO;: "Selective inhibition of mutant IDH1 by DS-1001b ameliorates aberrant histone modifications and impairs tumor activity in chondrosarcoma", ONCOGENE, NATURE PUBLISHING GROUP UK, LONDON, vol. 38, no. 42, 12 August 2019 (2019-08-12), London , pages 6835 - 6849, XP036906411, ISSN: 0950-9232, DOI: 10.1038/s41388-019-0929-9
KAZUHIDE ASHIZAWA: "Iyakuhin Kessho no Bunshi Jotai ni Kansuru Bussei Hyoka (12) Shio Kesshokei no Saitekika to Kesshoka Gijutsu [Physico-Chemical Studies on the Molecular Details of Drug Crystals]", PHARM TECH JAPAN, JIHO, INC., JP, vol. 18, no. 10, 1 January 2002 (2002-01-01), JP , pages 81 (1629) - 96 (1644), XP008177312, ISSN: 0910-4739
NORIYUKI TAKATA: "Cocrystal Screening and It Application in Improvement ofPhysicochemical Properties of APIs", PHARM TECH JAPAN, vol. 25, no. 12, 1 January 2009 (2009-01-01), JP , pages 155 - 166, XP009536191, ISSN: 0910-4739
T. W. GREENP.G.M. WUTS: "Protective Groups in Organic Synthesis", 2006, JOHN WILEY & SONS, INC.
Attorney, Agent or Firm:
CENTCREST IP ATTORNEYS (JP)
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