WO2011024039A1 - Synthèse de nouveaux dérivés 5-(2-(phénylsulfonyl)éthyl)-1h-indole - Google Patents

Synthèse de nouveaux dérivés 5-(2-(phénylsulfonyl)éthyl)-1h-indole Download PDF

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Publication number
WO2011024039A1
WO2011024039A1 PCT/IB2010/001886 IB2010001886W WO2011024039A1 WO 2011024039 A1 WO2011024039 A1 WO 2011024039A1 IB 2010001886 W IB2010001886 W IB 2010001886W WO 2011024039 A1 WO2011024039 A1 WO 2011024039A1
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WO
WIPO (PCT)
Prior art keywords
formula
product
scheme
ethyl
potassium carbonate
Prior art date
Application number
PCT/IB2010/001886
Other languages
English (en)
Inventor
Ramesh Babu Potluri
Hari Prasad Kodali
Srinivasa Rao Venturi
Venkata Srihari Tadimalla
Original Assignee
Ramesh Babu Potluri
Hari Prasad Kodali
Srinivasa Rao Venturi
Venkata Srihari Tadimalla
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 Ramesh Babu Potluri, Hari Prasad Kodali, Srinivasa Rao Venturi, Venkata Srihari Tadimalla filed Critical Ramesh Babu Potluri
Publication of WO2011024039A1 publication Critical patent/WO2011024039A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring

Definitions

  • An obji»ctive ⁇ Ftl ie present Invention is to develop commercially viable methods for the synthesis of 5- [(2-ph ⁇ yisulf m) )ethyl]-lH-lndole of formula II,
  • R 1 and R 2 arc the same Q ⁇ different and each independently
  • Another!I biij j,efetife of the present invention is to convert the product formula Il to formula I in high yields.
  • R 1 and R 2 arc the same or different and each independently represent a hydrogen, fluorine, or diflower alkyl)amtflo, acyi, or alkoxy caibonyl or chlorine atom, or a lower atkyl, lower alkoxy, nitro.
  • rya ⁇ , ⁇ minol ⁇ wer alkylamine group
  • R 5 is Acetyl, propyl, trlfluoacetyt,
  • inorganic base is selected from the group consisting sod liiuu ⁇ il cirbo , potassium carbonate or cesium carbonate and the organic base is selected from the gro uupp to ⁇ s iiisstti ig of triethylamine, diisopropytethylamine, N-meth ⁇ lmorpholine, pyridine, ⁇ -picoline, ⁇ - picolinb ⁇ i v-p co I ⁇ e.
  • a phas Ie t irans er catalyst is used, when an inorganic base is used.
  • the PTC is selected from the group consis nit ⁇ ft! of z ⁇ hriethylammo ⁇ ium chloride, tetrabut ⁇ lar ⁇ r ⁇ o ⁇ ium bromide, tetrob ⁇ tylammonium hydrogeri lsulp ia1 e, 15 Crown 5 or 10 Crown 6.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)

Abstract

L'objectif de la présente invention est de développer commercialement des procédés viables pour la synthèse de 5-[2-phénylsulfony)éthyl]-1H-indole de formule (II), R1 et R2 étant identiques ou différents et chacun représentant indépendamment un hydrogène, un fluor, ou un di(alkyle inférieur)amino, un acyle, ou un alcoxy carbonyle ou un atome de chlore, ou un alkyle inférieur, un alcoxy inférieur, un nitro, un cyano, un groupe alkylamine amino inférieur de formule (II). Un autre objectif de la présente invention est de convertir le produit formule (II) en formule (I) à haut rendement, R1 et R2 étant identiques ou différents et chacun représentant indépendamment un hydrogène, un fluor, ou un di(alkyle inférieur)amino, un acyle, ou un alkoxy carbonyle ou un atome de chlore, ou un alkyle inférieur, un alcoxy inférieur, un nitro, un cyano, un groupe alkylamine amino inférieur de formule (I). L'un des premiers procédés utilisé fut par réaction du dérivé d'indole de formule (III) avec des sulfones aryliques vinyliques de formule (V) tel qu'illustré dans le schéma III. Un autre procédé utilisé fut par réaction du dérivé d'aniline de formule (VI) avec des sulfones aryle de formule (VII) tel qu'illustré dans les schémas III et IV.
PCT/IB2010/001886 2009-08-25 2010-07-30 Synthèse de nouveaux dérivés 5-(2-(phénylsulfonyl)éthyl)-1h-indole WO2011024039A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2030/CHE/2009 2009-08-25
IN2030CH2009 2009-08-25

Publications (1)

Publication Number Publication Date
WO2011024039A1 true WO2011024039A1 (fr) 2011-03-03

Family

ID=43627318

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2010/001886 WO2011024039A1 (fr) 2009-08-25 2010-07-30 Synthèse de nouveaux dérivés 5-(2-(phénylsulfonyl)éthyl)-1h-indole

Country Status (1)

Country Link
WO (1) WO2011024039A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992006973A1 (fr) * 1990-10-15 1992-04-30 Pfizer Inc. Derives d'indole
US5545644A (en) * 1990-10-15 1996-08-13 Pfizer Inc. Indole derivatives
EP1088817A2 (fr) * 1999-10-01 2001-04-04 Pfizer Limited Procédé pour la préparation de 3-acyl-indoles
WO2002050063A1 (fr) * 2000-12-20 2002-06-27 Pfizer Limited Nouveau procede

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992006973A1 (fr) * 1990-10-15 1992-04-30 Pfizer Inc. Derives d'indole
US5545644A (en) * 1990-10-15 1996-08-13 Pfizer Inc. Indole derivatives
EP1088817A2 (fr) * 1999-10-01 2001-04-04 Pfizer Limited Procédé pour la préparation de 3-acyl-indoles
WO2002050063A1 (fr) * 2000-12-20 2002-06-27 Pfizer Limited Nouveau procede

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