Title:
PREPARATION METHOD FOR C3-ALKYLATED INDOLE
Document Type and Number:
WIPO Patent Application WO/2023/142231
Kind Code:
A1
Abstract:
A preparation method for C3-alkylated indole, in which elemental iodine is used as a catalyst, silane is used as a reducing agent and a carbonyl compound is used as an alkylation reagent, and the C3-alkylated indole is prepared under mild conditions. The present method does not need toxic and harmful metal reagents and has mild reaction conditions, uses a cheap catalyst with a low dosage and is convenient in post-treatment, thus facilitating the application to drug molecular synthesis. The method has few reaction steps, does not need a ligand and can prepare a target compound just by a one-step reaction, thus satisfying the demand and direction of green chemistry.
Inventors:
WAN XIAOBING (CN)
CHENG XIONGLUE (CN)
WANG LILI (CN)
LIU YIDE (CN)
JIANG GANGZHONG (CN)
TAO SUYAN (CN)
WAN XIAO (CN)
LI RUYI (CN)
XIANG ZIXIN (CN)
CHENG XIONGLUE (CN)
WANG LILI (CN)
LIU YIDE (CN)
JIANG GANGZHONG (CN)
TAO SUYAN (CN)
WAN XIAO (CN)
LI RUYI (CN)
XIANG ZIXIN (CN)
Application Number:
PCT/CN2022/079805
Publication Date:
August 03, 2023
Filing Date:
March 08, 2022
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07D209/86; C07B37/00; C07D401/12; C07D405/06; C07D409/06; C07D413/06; C07D471/06
Foreign References:
| CN1252794A | 2000-05-10 | |||
| CN101506159A | 2009-08-12 |
Other References:
NOLAND, WAYLAND E. ET AL.: "3-(Indolyl)-Phthalides and (2-Carboxybenzyl)-Indoles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 82, 5 October 1960 (1960-10-05), pages 5143 - 5147, XP055851445
ZHANG TIANZE, YU MIN, HUANG HANMIN: "Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 12, no. 31, 11 August 2021 (2021-08-11), United Kingdom , pages 10501 - 10505, XP093082199, ISSN: 2041-6520, DOI: 10.1039/D1SC03058B
KHAN IMRAN, SHARMA AANCHAL, KAMBOJ PRIYA, MAITY BANIBRATA, TYAGI VIKAS: "Base‐Mediated Reductive Coupling of Indole‐3‐tosylhydrazone with Thiols/Boronic Acids: Facile Synthesis of 3‐(phenylthio)methyl/benzyl Indole Derivatives", CHEMISTRYSELECT, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 5, no. 2, 16 January 2020 (2020-01-16), DE , pages 591 - 600, XP093082202, ISSN: 2365-6549, DOI: 10.1002/slct.201903863
FRIDKIN GIL, BOUTARD NICOLAS, LUBELL WILLIAM D.: "β,β-Disubstituted C - and N -Vinylindoles from One-Step Condensations of Aldehydes and Indole Derivatives", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 74, no. 15, 7 August 2009 (2009-08-07), pages 5603 - 5606, XP093082204, ISSN: 0022-3263, DOI: 10.1021/jo900526p
LIEJIN ZHOU; BING XU; JUNLIANG ZHANG: "Metal‐Free Dehydrogenative Diels–Alder Reactions of 2‐Methyl‐3‐Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 54, no. 31, 10 June 2015 (2015-06-10), Hoboken, USA, pages 9092 - 9096, XP072068311, ISSN: 1433-7851, DOI: 10.1002/anie.201503549
NOMIYAMA, SHOTA ET AL.: "Easy Access to a Library of Alkylindoles: Reductive Alkylation of Indoles with Carbonyl Compounds and Hydrosilanes under Indium Catalysis", ADVANCED SYNTHESIS & CATALYSIS, vol. 358, 3 March 2016 (2016-03-03), pages 1136 - 1149, XP072357297, DOI: 10.1002/adsc.201500502
KIM WEONJEONG, KOO JANGWOO, LEE HONG GEUN: "Benzylic C(sp 3 )–C(sp 2 ) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 12, no. 11, 25 March 2021 (2021-03-25), United Kingdom , pages 4119 - 4125, XP093082207, ISSN: 2041-6520, DOI: 10.1039/D0SC06666D
MARTÍNEZ-LARA FERNANDO, SUÁREZ ANISLEY, SUÁREZ-PANTIGA SAMUEL, TAPIA M. JOSÉ, SANZ ROBERTO: "Straight access to highly fluorescent angular indolocarbazoles via merging Au- and Mo-catalysis", ORGANIC CHEMISTRY FRONTIERS, vol. 7, no. 14, 14 July 2020 (2020-07-14), pages 1869 - 1877, XP093082208, DOI: 10.1039/D0QO00405G
LIU WEN-BO, SCHUMAN DAVID P., YANG YUN-FANG, TOUTOV ANTON A., LIANG YONG, KLARE HENDRIK F. T., NESNAS NASRI, OESTREICH MARTIN, BLA: "Potassium tert -Butoxide-Catalyzed Dehydrogenative C–H Silylation of Heteroaromatics: A Combined Experimental and Computational Mechanistic Study", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 139, no. 20, 24 May 2017 (2017-05-24), pages 6867 - 6879, XP093082210, ISSN: 0002-7863, DOI: 10.1021/jacs.6b13031
ZHANG TIANZE, YU MIN, HUANG HANMIN: "Fe-catalyzed Fukuyama-type indole synthesis triggered by hydrogen atom transfer", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 12, no. 31, 11 August 2021 (2021-08-11), United Kingdom , pages 10501 - 10505, XP093082199, ISSN: 2041-6520, DOI: 10.1039/D1SC03058B
KHAN IMRAN, SHARMA AANCHAL, KAMBOJ PRIYA, MAITY BANIBRATA, TYAGI VIKAS: "Base‐Mediated Reductive Coupling of Indole‐3‐tosylhydrazone with Thiols/Boronic Acids: Facile Synthesis of 3‐(phenylthio)methyl/benzyl Indole Derivatives", CHEMISTRYSELECT, WILEY - V C H VERLAG GMBH & CO. KGAA, DE, vol. 5, no. 2, 16 January 2020 (2020-01-16), DE , pages 591 - 600, XP093082202, ISSN: 2365-6549, DOI: 10.1002/slct.201903863
FRIDKIN GIL, BOUTARD NICOLAS, LUBELL WILLIAM D.: "β,β-Disubstituted C - and N -Vinylindoles from One-Step Condensations of Aldehydes and Indole Derivatives", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 74, no. 15, 7 August 2009 (2009-08-07), pages 5603 - 5606, XP093082204, ISSN: 0022-3263, DOI: 10.1021/jo900526p
LIEJIN ZHOU; BING XU; JUNLIANG ZHANG: "Metal‐Free Dehydrogenative Diels–Alder Reactions of 2‐Methyl‐3‐Alkylindoles with Dienophiles: Rapid Access to Tetrahydrocarbazoles, Carbazoles, and Heteroacenes", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 54, no. 31, 10 June 2015 (2015-06-10), Hoboken, USA, pages 9092 - 9096, XP072068311, ISSN: 1433-7851, DOI: 10.1002/anie.201503549
NOMIYAMA, SHOTA ET AL.: "Easy Access to a Library of Alkylindoles: Reductive Alkylation of Indoles with Carbonyl Compounds and Hydrosilanes under Indium Catalysis", ADVANCED SYNTHESIS & CATALYSIS, vol. 358, 3 March 2016 (2016-03-03), pages 1136 - 1149, XP072357297, DOI: 10.1002/adsc.201500502
KIM WEONJEONG, KOO JANGWOO, LEE HONG GEUN: "Benzylic C(sp 3 )–C(sp 2 ) cross-coupling of indoles enabled by oxidative radical generation and nickel catalysis", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 12, no. 11, 25 March 2021 (2021-03-25), United Kingdom , pages 4119 - 4125, XP093082207, ISSN: 2041-6520, DOI: 10.1039/D0SC06666D
MARTÍNEZ-LARA FERNANDO, SUÁREZ ANISLEY, SUÁREZ-PANTIGA SAMUEL, TAPIA M. JOSÉ, SANZ ROBERTO: "Straight access to highly fluorescent angular indolocarbazoles via merging Au- and Mo-catalysis", ORGANIC CHEMISTRY FRONTIERS, vol. 7, no. 14, 14 July 2020 (2020-07-14), pages 1869 - 1877, XP093082208, DOI: 10.1039/D0QO00405G
LIU WEN-BO, SCHUMAN DAVID P., YANG YUN-FANG, TOUTOV ANTON A., LIANG YONG, KLARE HENDRIK F. T., NESNAS NASRI, OESTREICH MARTIN, BLA: "Potassium tert -Butoxide-Catalyzed Dehydrogenative C–H Silylation of Heteroaromatics: A Combined Experimental and Computational Mechanistic Study", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 139, no. 20, 24 May 2017 (2017-05-24), pages 6867 - 6879, XP093082210, ISSN: 0002-7863, DOI: 10.1021/jacs.6b13031
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
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