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-

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• 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)

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• 2006
  • 2006-06-28 CN CNA2006800240776A patent/CN101213172A/zh active Pending
  • 2006-06-28 WO PCT/US2006/025143 patent/WO2007005454A2/en active Application Filing
  • 2006-06-28 JP JP2008519514A patent/JP2008544987A/ja not_active Withdrawn
  • 2006-06-28 EP EP06774178A patent/EP1902023A4/de not_active Withdrawn
  • 2006-06-29 TW TW095123584A patent/TW200800955A/zh unknown
• 2007
  • 2007-12-19 IL IL188238A patent/IL188238A0/en unknown

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