WO2005090302A3 - Palladium catalyzed indolization of 2-bromo or chloroanilines - Google Patents

Palladium catalyzed indolization of 2-bromo or chloroanilines Download PDF

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Publication number
WO2005090302A3
WO2005090302A3 PCT/US2005/008620 US2005008620W WO2005090302A3 WO 2005090302 A3 WO2005090302 A3 WO 2005090302A3 US 2005008620 W US2005008620 W US 2005008620W WO 2005090302 A3 WO2005090302 A3 WO 2005090302A3
Authority
WO
WIPO (PCT)
Prior art keywords
chloroanilines
bromo
palladium catalyzed
formula
indolization
Prior art date
Application number
PCT/US2005/008620
Other languages
French (fr)
Other versions
WO2005090302A2 (en
Inventor
Guisheng Li
Jianxiu Liu
Zhi-Hui Lu
Frank Roschangar
Chris Hugh Senanayake
Ming Shen
Original Assignee
Boehringer Ingelheim Int
Guisheng Li
Jianxiu Liu
Zhi-Hui Lu
Frank Roschangar
Chris Hugh Senanayake
Ming Shen
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Boehringer Ingelheim Int, Guisheng Li, Jianxiu Liu, Zhi-Hui Lu, Frank Roschangar, Chris Hugh Senanayake, Ming Shen filed Critical Boehringer Ingelheim Int
Priority to EP05725655A priority Critical patent/EP1727796A2/en
Priority to JP2007504038A priority patent/JP4879160B2/en
Priority to CA2558051A priority patent/CA2558051C/en
Publication of WO2005090302A2 publication Critical patent/WO2005090302A2/en
Publication of WO2005090302A3 publication Critical patent/WO2005090302A3/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/38Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12Radicals substituted by oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/04Systems containing only non-condensed rings with a four-membered ring

Abstract

The present invention provides a method for making substituted indole compounds of general formula III comprising the step of: (a) reacting a 2-bromoaniline or 2-chloroaniline of general formula (I); wherein: X, R and R1 are defined herein with a substituted acetylene of formula (II); wherein R2 and R3 in the presence of a palladium catalyst, a ligand, and a base in a solvent at a suitable temperature to give a compound of formula (III)
PCT/US2005/008620 2004-03-16 2005-03-14 Palladium catalyzed indolization of 2-bromo or chloroanilines WO2005090302A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP05725655A EP1727796A2 (en) 2004-03-16 2005-03-14 Palladium catalyzed indolization of 2-bromo or chloroanilines
JP2007504038A JP4879160B2 (en) 2004-03-16 2005-03-14 Palladium-catalyzed indolization of 2-bromo or chloroaniline
CA2558051A CA2558051C (en) 2004-03-16 2005-03-14 Palladium catalyzed indolization of 2-bromo or chloroanilines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US55359604P 2004-03-16 2004-03-16
US60/553,596 2004-03-16

Publications (2)

Publication Number Publication Date
WO2005090302A2 WO2005090302A2 (en) 2005-09-29
WO2005090302A3 true WO2005090302A3 (en) 2006-07-13

Family

ID=34994422

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/008620 WO2005090302A2 (en) 2004-03-16 2005-03-14 Palladium catalyzed indolization of 2-bromo or chloroanilines

Country Status (5)

Country Link
US (2) US7126009B2 (en)
EP (1) EP1727796A2 (en)
JP (1) JP4879160B2 (en)
CA (1) CA2558051C (en)
WO (1) WO2005090302A2 (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2335700A1 (en) * 2001-07-25 2011-06-22 Boehringer Ingelheim (Canada) Ltd. Hepatitis C virus polymerase inhibitors with a heterobicylic structure
US7098231B2 (en) * 2003-01-22 2006-08-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
US7223785B2 (en) * 2003-01-22 2007-05-29 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
CN101648944A (en) * 2004-02-20 2010-02-17 贝林格尔.英格海姆国际有限公司 Viral polymerase inhibitors
AU2006204917A1 (en) * 2005-01-14 2006-07-20 Smithkline Beecham Corporation Indole derivatives for treating viral infections
KR20070112165A (en) * 2005-02-11 2007-11-22 베링거 인겔하임 인터내셔날 게엠베하 Process for preparing 2,3-disubstituted indoles
JP5015154B2 (en) * 2005-08-12 2012-08-29 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング Viral polymerase inhibitor
AU2006279537A1 (en) * 2005-08-15 2007-02-22 Irm Llc Compounds and compositions as TPO mimetics
US20080051384A1 (en) * 2006-07-14 2008-02-28 Genelabs Technologies, Inc. Antiviral agents
AR072297A1 (en) * 2008-06-27 2010-08-18 Novartis Ag DERIVATIVES OF INDOL-2-IL-PIRIDIN-3-ILO, PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND ITS USE IN MEDICINES FOR THE TREATMENT OF DISEASES MEDIATED BY THE SYNTHESIS ALDOSTERONE.
CN113527173B (en) * 2021-08-30 2022-12-16 河南师范大学 Method for synthesizing indole terpene analogues through Heck tandem reaction

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB427251A (en) * 1933-08-18 1935-04-18 Ici Ltd Manufacture of intermediates for dyes
US3905999A (en) * 1972-06-20 1975-09-16 Eastman Kodak Co Synthesis of 2,3-substituted indoles
KR950701317A (en) * 1992-05-08 1995-03-23 오오쓰까 아끼히꼬 Indole Derivative
US6028111A (en) * 1996-03-08 2000-02-22 Oxigene, Inc. Compositions and use of benzamides and nicotinamides as anti-inflammatory agents
EP2335700A1 (en) * 2001-07-25 2011-06-22 Boehringer Ingelheim (Canada) Ltd. Hepatitis C virus polymerase inhibitors with a heterobicylic structure

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
DATABASE ZREGISTRY [online] 12 December 1987 (1987-12-12), XP002377297, retrieved from STN *
DATABASE ZREGISTRY [online] 16 November 1984 (1984-11-16), XP002377298, retrieved from STN *
DATABASE ZREGISTRY [online] 16 November 1984 (1984-11-16), XP002377299, retrieved from STN *
F. MAASSARANI, M. PFEFFER, J. SPENCER, E. WEHMAN, JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 466, 1994, pages 265 - 271, XP002375385 *
FIDA MAASSARANI, MICHEL PFEFFER, GUY LE BORGNE, ORGANOMETALLICS, vol. 6, 1987, pages 2029 - 2043, XP002375383 *
FIDA MAASSARANI, MICHEL PFEFFER, GUY LE BORGNE, ORGANOMETALLICS, vol. 6, 1987, pages 2043 - 2053, XP002375384 *
ORGANIC LETTERS, vol. 6, no. 22, 2004, pages 4129 - 4132, XP002375386 *
R. C. LAROCK, E. K. YUM, M. D. REFVIK, J. ORG. CHEM., vol. 63, 1998, pages 7652 - 7662, XP002375382 *

Also Published As

Publication number Publication date
EP1727796A2 (en) 2006-12-06
WO2005090302A2 (en) 2005-09-29
CA2558051A1 (en) 2005-09-29
JP2007529538A (en) 2007-10-25
US20060287376A1 (en) 2006-12-21
US7408076B2 (en) 2008-08-05
CA2558051C (en) 2013-03-12
JP4879160B2 (en) 2012-02-22
US20050209465A1 (en) 2005-09-22
US7126009B2 (en) 2006-10-24

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