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WO2020026260A1 - Nouveaux composés de 2-(3-halo-5-méthyl-1h-pyrazol-1-yl)-3-halopyridine et leurs intermédiaires - Google Patents

Nouveaux composés de 2-(3-halo-5-méthyl-1h-pyrazol-1-yl)-3-halopyridine et leurs intermédiaires Download PDF

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Publication number
WO2020026260A1
WO2020026260A1 PCT/IN2019/000021 IN2019000021W WO2020026260A1 WO 2020026260 A1 WO2020026260 A1 WO 2020026260A1 IN 2019000021 W IN2019000021 W IN 2019000021W WO 2020026260 A1 WO2020026260 A1 WO 2020026260A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compound
doublet
stretch
halo
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/IN2019/000021
Other languages
English (en)
Inventor
Rajendra Pralhad Chaudhari
Vandana Chandrakant Mhatre
Rajendra Ramdas GHARTE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical India Ltd
Original Assignee
Sumitomo Chemical India Ltd
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 Sumitomo Chemical India Ltd filed Critical Sumitomo Chemical India Ltd
Publication of WO2020026260A1 publication Critical patent/WO2020026260A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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
    • C07D401/04—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C07D213/77—Hydrazine radicals

Definitions

  • This invention relates to novel 2-(3-halo-5-methyl- JiT-pyrazol- l-yl)-3- halopyridine compounds and intermediates thereof, process for preparation and use. More specifically, present invention relates to title compounds, use and preparation starting from crotonoyl halide and 3-halo-2-hydrazinyl pyridine.
  • Novel 2-(3-halo-5-methyl- i/i-pyrazol- l-yl)-3-halopyridines and intermediates thereof are not reported in the literature.
  • Said halopyridine compounds are useful chemical-intermediates which are prepared from commercially available raw materials.
  • Main object of invention is to provide novel 2-(3-halo-5-methyl- I/f- pyrazol-l-yl)-3-halopyridine compounds and intermediates thereof.
  • Another object of invention is to provide method of preparation of 2- (3-halo-5-methyl- JH-pyra2ol- l-yl)-3-halopyridine compounds and intermediates thereof.
  • Yet another object of invention is to disclose use of novel 2-(3-halo-5- methyl- IH-pyrazol-l-yl)-3-halopyridine compounds for preparation of chemical intermediates useful in synthesis of pesticides.
  • Title compounds are prepared from crotonoyl halide and 3-halo-2- hydrazinyl pyridine.
  • 3-Halo-2-hydrazinyl pyridine is reacted with crotonoyl halide in presence of an acid acceptor to produce lV -(3-halopyridin-2-yl)-2- alkenehydrazide as shown below:
  • Preferred acid acceptors are alkali metal bicarbonates. Most preferred acid acceptor is sodium bicarbonate.
  • Compound of Formula (III) reacts with phosphorus oxyhalide to form compound of Formula (IV) wherein R is a halogen which is same or different as R 1 .
  • D2O Exchangeable protons 7.5246, 1H, singlet, -NH, 9.6506, 1H, singlet, -NH.
  • UV spectra 205 nm, 254nm
  • UV spectra 206 nm, 276nm
  • UV spectra 211nm, 242nm, 271nm.
  • Example-5 The product obtained in Example-5 was used as described in Example-6 below to prepare 3-bromo- l-(3-chloropyridin-2-yl)- li : /- pyrazole-5 -carboxylic acid which is an intermediate in the synthesis of pesticides.
  • UV spectra 216nm, 266nm.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux composés de 2-(3-halo-5-méthyl-1H-pyrazol-1-yl)-3-halopyridine et leurs intermédiaires. L'invention concerne également un procédé de préparation desdits composés. Les composés de l'invention sont utiles en tant qu'intermédiaires chimiques.
PCT/IN2019/000021 2018-07-31 2019-07-18 Nouveaux composés de 2-(3-halo-5-méthyl-1h-pyrazol-1-yl)-3-halopyridine et leurs intermédiaires Ceased WO2020026260A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN201821028738 2018-07-31
IN201821028738 2018-07-31

Publications (1)

Publication Number Publication Date
WO2020026260A1 true WO2020026260A1 (fr) 2020-02-06

Family

ID=69232401

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2019/000021 Ceased WO2020026260A1 (fr) 2018-07-31 2019-07-18 Nouveaux composés de 2-(3-halo-5-méthyl-1h-pyrazol-1-yl)-3-halopyridine et leurs intermédiaires

Country Status (1)

Country Link
WO (1) WO2020026260A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020212991A1 (fr) * 2019-04-19 2020-10-22 Adama Makhteshim Ltd. Préparation de pyrazoles substitués et leur utilisation en tant que précurseurs d'anthranilamides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070203342A1 (en) * 2001-08-13 2007-08-30 Freudenberger John H Subtituted dihydro 3-halo-1H-pyrazole-5-carboxylates their preparation and use
WO2008126933A2 (fr) * 2007-04-11 2008-10-23 Sumitomo Chemical Company, Limited Procédé de production de composé amide
US20100113794A1 (en) * 2007-04-11 2010-05-06 Yoshihiko Nokura Method for producing amide compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070203342A1 (en) * 2001-08-13 2007-08-30 Freudenberger John H Subtituted dihydro 3-halo-1H-pyrazole-5-carboxylates their preparation and use
WO2008126933A2 (fr) * 2007-04-11 2008-10-23 Sumitomo Chemical Company, Limited Procédé de production de composé amide
US20100113794A1 (en) * 2007-04-11 2010-05-06 Yoshihiko Nokura Method for producing amide compound

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020212991A1 (fr) * 2019-04-19 2020-10-22 Adama Makhteshim Ltd. Préparation de pyrazoles substitués et leur utilisation en tant que précurseurs d'anthranilamides
US12459913B2 (en) 2019-04-19 2025-11-04 Adama Makhteshim Ltd. Preparation of substituted pyrazoles and their use as anthranilamides precursors

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