EP1902023A4 - Procede ameliore pour preparer des heterocycles insecticides substitues par phenylalkyle (propenyle disubstitue) - Google Patents

Procede ameliore pour preparer des heterocycles insecticides substitues par phenylalkyle (propenyle disubstitue)

Info

Publication number
EP1902023A4
EP1902023A4 EP06774178A EP06774178A EP1902023A4 EP 1902023 A4 EP1902023 A4 EP 1902023A4 EP 06774178 A EP06774178 A EP 06774178A EP 06774178 A EP06774178 A EP 06774178A EP 1902023 A4 EP1902023 A4 EP 1902023A4
Authority
EP
European Patent Office
Prior art keywords
optionally substituted
formula
alkyl
compound
halogen
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.)
Withdrawn
Application number
EP06774178A
Other languages
German (de)
English (en)
Other versions
EP1902023A2 (fr
Inventor
Jaidev S Goudar
Charles E Hatch Iii
Guozhi Wang
Russell Patera
Craig A Polsz
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.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1902023A2 publication Critical patent/EP1902023A2/fr
Publication of EP1902023A4 publication Critical patent/EP1902023A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/58—One oxygen atom, e.g. butenolide
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6

Definitions

  • R 5 is an optionally substituted heterocyclic ring group, provided that
  • R 5 is not an optionally substituted dihydrobenzofuran; and x is 2, 3, 4, 5 or 6;
  • R 5 is as defined above;
  • R 6 and R 7 are independently selected from halogen, hydroxyl or -OSO 2 R 8 wherein R 8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
  • R 5 , R 7 and x are as defined above;
  • R 3 and R 4 are as defined above;
  • the "about” range shall be not more than 10% of the absolute value of an end point or 10% of the range recited, whichever is less.
  • alkyl As used in this specification and unless otherwise indicated the substituent terms "alkyl”, “alkenyl”, “alkoxy”, and “haloalkyl”, used alone or as part of a larger moiety, includes straight or branched chains of at least one or two carbon atoms, as appropriate to the substituent, and preferably up to 12 carbon atoms, more preferably up to ten carbon atoms, most preferably up to seven carbon atoms, wherein “alkenyl” has at least one carbon to carbon double bond.
  • Halogen “halide” or “halo” refers to fluorine, bromine, iodine, or chlorine.
  • ambient temperature refers to a temperature in the range of about 20° C to about 30° C.
  • the present invention relates to a process for preparing a compound of formula I:
  • R 5 is an optionally substituted heterocyclic ring group, provided that
  • R 5 is not an optionally substituted dihydrobenzofuran; and x is 2, 3, 4, 5 or 6;
  • R 5 is as defined above;
  • R 6 and R 7 are independently selected from halogen, hydroxyl or -OSO 2 R 8 wherein R 8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6;
  • R 5 , R 7 and x are as defined above;
  • R and R are as defined above;
  • the reacting of step a) can be conducted in the presence of a catalyst; at elevated temperature.
  • the catalyst can be polyethylene glycol, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof.
  • the catalyst can be present in a concentration of from about 0.1% by weight to about 15% by weight.
  • the elevated temperature can be in the range of 30°C to 120°C.
  • the reaction of step b) can be conducted in the presence of a solvent; in the presence of a catalyst; at elevated temperature.
  • the solvent can be tetrahydrofuran, toluene, xylene, 1,2-dichloroethane, triethylamine, j ⁇ -dioxane, N 5 N- dimethylacetamide, N,N-dimethylformamide, glymes, methyl isobutyl ketone, dimethylsulfoxide or mixtures thereof.
  • the catalyst can be polyethylene glycol, potassium iodide, triethylamine, pyridine, phase transfer catalysts such as quaternary ammonium salts or quaternary phosphonium salts or mixtures thereof.
  • the catalyst can be present in a concentration of from about 0.1 % by weight to about 20% by weight.
  • the elevated temperature can be in the range of 30°C to 70°C.
  • R 5 is an optionally substituted heterocyclic ring group, provided that R 5 is not an optionally substituted dihydrobenzofuran; R is selected from halogen, hydroxyl or -OSO 2 R wherein R 8 is alkyl or aryl; and x is 2, 3, 4, 5 or 6.
  • the heterocyclic ring in the optionally substituted heterocyclic ring group is preferably selected from the group consisting of isoxazole, thiazole, 1,3,4- thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,2,3-triazole, 1,2,4- triazole, 1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine, 1,3,5-triazine, indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, diox
  • the optional substitutent on the optionally substituted heterocyclic ring group is preferably selected from the group consisting of halogen, nitro, cyano, alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfmyl, alkylsulfonyl, haloalkylsulflnyl, haloalkylsulfonyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, amino, dimethylamino, acetamido, acetyl, haloacetyl, formyl, carboxyl, methoxycarbonyl, cycloalkyl, (alkyl)aminocarbonyl, [di(alkyl)amino]carbonyl, optionally substituted phenyl, optionally substituted benzyl, optionally substituted phenoxy,
  • R 5 is benzofuran wherein R 6 and R 7 are halogen ⁇
  • step (b) of Example 1 2,6-dihalo-4-(phenylmethoxy)phenol, a compound of formula (C), is reacted with a l-(benzo[2,3-b]furan-7-yloxy)-4-haloalkane, a compound of formula II, for example l-(benzo[2,3-b]furan-7-yloxy)-4-halobutane, in the presence of a base, a solvent and a catalyst at elevated temperature to form a 7- ⁇ 4-[2,6-dihalo-4-(phenylmethoxy)phenoxy]alkoxy ⁇ benzo[b]furan, a compound of formula I, for example 7- ⁇ 4-[2,6-dihalo-4-(phenylmethoxy)phenoxy]butoxy ⁇ benzo[b]furan.
  • a compound of formula II for example l-(benzo[2,3-b]furan-7-yloxy)-4-halobutane
  • R 5 is a wherein R 6 and R 7 are halogen ⁇ substituted pyridine; Y is CF,
  • R 3 and R 4 are halogen wherein R 7 is halogen
  • step (b) of Example 2 2,6-dihalo-4-(phenylmethoxy)phenol, a compound of formula (C), is reacted with a 1 -(substituted pyridin-2-yloxy)-4-haloalkane, a compound of formula II, for example l-((5-trifluoromethyl)pyridin-2-yloxy)-4- halobutane, in the presence of a base, a solvent and a catalyst at elevated temperature to form a 2- ⁇ 4-[2,6-dihalo-4-

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)

Abstract

L'invention concerne un procédé amélioré permettant de préparer des hétérocycles substitués de phénylalkyle (propényle disubstitué). Ce procédé amélioré est centré sur des étapes pour produire des produits intermédiaires clefs, en particulier des composés de formule (I) dans laquelle R3, R4, R5 et x sont définis ici.
EP06774178A 2005-06-30 2006-06-28 Procede ameliore pour preparer des heterocycles insecticides substitues par phenylalkyle (propenyle disubstitue) Withdrawn EP1902023A4 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US69529505P 2005-06-30 2005-06-30
PCT/US2006/025143 WO2007005454A2 (fr) 2005-06-30 2006-06-28 Procede ameliore pour preparer des heterocycles insecticides substitues par phenylalkyle (propenyle disubstitue)

Publications (2)

Publication Number Publication Date
EP1902023A2 EP1902023A2 (fr) 2008-03-26
EP1902023A4 true EP1902023A4 (fr) 2009-08-12

Family

ID=37604978

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06774178A Withdrawn EP1902023A4 (fr) 2005-06-30 2006-06-28 Procede ameliore pour preparer des heterocycles insecticides substitues par phenylalkyle (propenyle disubstitue)

Country Status (6)

Country Link
EP (1) EP1902023A4 (fr)
JP (1) JP2008544987A (fr)
CN (1) CN101213172A (fr)
IL (1) IL188238A0 (fr)
TW (1) TW200800955A (fr)
WO (1) WO2007005454A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011149694A1 (fr) 2010-05-26 2011-12-01 Corning Incorporated Échange d'ions de verre à revêtement antireflet ar et procédé associé

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3933837A (en) * 1973-07-23 1976-01-20 Sterling Drug Inc. 3,4-Methylenedioxyphenoxy-alkyl diketones and keto-esters
US5599815A (en) * 1993-02-04 1997-02-04 Meiji Seika Kabushiki Kaisha Antipsychotic benzoisothiazolyl piperazine derivatives
US5922880A (en) * 1994-10-14 1999-07-13 Sumitomo Chemical Company, Limited Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production
US6090836A (en) * 1996-02-02 2000-07-18 Merck & Co., Inc. Benzisoxazole-derived antidiabetic compounds
US20020086891A1 (en) * 2000-11-02 2002-07-04 Johannes Aebi Heteroaromate OSC inhibitors
WO2004011448A1 (fr) * 2002-07-25 2004-02-05 Merck & Co., Inc. Composes therapeutiques destines au traitement d'etats dyslipidemiques
EP1396490A1 (fr) * 2001-05-24 2004-03-10 Yamanouchi Pharmaceutical Co. Ltd. Derives de 3-quinoleine-2-(1h)-ylideneindoline-2-one
WO2004098284A2 (fr) * 2003-04-30 2004-11-18 Fmc Corporation Derives pesticides de benzodioxolane et de benzodioxole a substitution (dihalopropenyl)phenylalkyle

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW499412B (en) * 1996-11-26 2002-08-21 Dimensional Pharm Inc Aminoguanidines and alkoxyguanidines as protease inhibitors

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3933837A (en) * 1973-07-23 1976-01-20 Sterling Drug Inc. 3,4-Methylenedioxyphenoxy-alkyl diketones and keto-esters
US5599815A (en) * 1993-02-04 1997-02-04 Meiji Seika Kabushiki Kaisha Antipsychotic benzoisothiazolyl piperazine derivatives
US5922880A (en) * 1994-10-14 1999-07-13 Sumitomo Chemical Company, Limited Dihalopropene compounds, insecticidal/acaricidal agents containing same, and intermediates for their production
US6090836A (en) * 1996-02-02 2000-07-18 Merck & Co., Inc. Benzisoxazole-derived antidiabetic compounds
US20020086891A1 (en) * 2000-11-02 2002-07-04 Johannes Aebi Heteroaromate OSC inhibitors
EP1396490A1 (fr) * 2001-05-24 2004-03-10 Yamanouchi Pharmaceutical Co. Ltd. Derives de 3-quinoleine-2-(1h)-ylideneindoline-2-one
WO2004011448A1 (fr) * 2002-07-25 2004-02-05 Merck & Co., Inc. Composes therapeutiques destines au traitement d'etats dyslipidemiques
WO2004098284A2 (fr) * 2003-04-30 2004-11-18 Fmc Corporation Derives pesticides de benzodioxolane et de benzodioxole a substitution (dihalopropenyl)phenylalkyle

Also Published As

Publication number Publication date
IL188238A0 (en) 2008-04-13
JP2008544987A (ja) 2008-12-11
CN101213172A (zh) 2008-07-02
EP1902023A2 (fr) 2008-03-26
WO2007005454A2 (fr) 2007-01-11
WO2007005454A3 (fr) 2007-05-03
TW200800955A (en) 2008-01-01

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