Methods for preparing 5- and 6-benzyl-functionalized quinoxalines
OwnerJuan Jesus Burdeniucinventor
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Abstract
The present invention pertains to methods for preparing 5- and 6-benzyl functionalized quinoxalines. In a first embodiment, the method comprises contacting an aqueous suspension of a 5- and 6-halomethyl quinoxaline with a water-soluble nucleophile. In a second embodiment, the method comprises contacting a 5- and 6-halomethyl quinoxaline with an organic solvent-soluble nucleophile in an inert polar organic solvent. In a third embodiment, the method comprises contacting a 5- and 6-halomethyl quinoxaline in an organic solvent with an aqueous solution of a water-soluble nucleophile in the presence of a phase transfer catalyst.
Claims32
A method for preparing a compound having Formula (I)
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- which comprises contacting an aqueous suspension of a compound having Formula (II) with a water-soluble nucleophile, N1, containing moiety Y;
- wherein X is chloro or bromo;
- R1 is selected from the group consisting of hydrogen and branched and unbranched alkyl and aryl groups having from 1 to 9 carbon atoms;
- Y is selected from the group consisting of —OR2, —NHR2, —NR2R3, —SR2, and —CN;
- and R2 and R3are independently selected from the group consisting of hydrogen and branched and unbranched alkyl groups having from 1 to 4 carbon atoms.
A method for preparing a compound having Formula (I)
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- which comprises contacting a compound having Formula (II) with an organic solvent-soluble nucleophile, N2, containing moiety Y, in an inert polar organic solvent;
- wherein X is chloro or bromo;
- R1 is selected from the group consisting of hydrogen and branched and unbranched alkyl and aryl groups having from 1 to 9 carbon atoms;
- Y is selected from the group consisting of —OR2, —NHR2, —NR2R3, and —SR2;
- and R2 and R3 are independently selected from the group consisting of hydrogen and branched and unbranched alkyl and aryl groups having from 5 to 9 carbon atoms.
A method for preparing a compound having Formula (I)
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- which comprises contacting a compound having Formula (II) in an organic solvent with an aqueous solution of a water-soluble nucleophile, N1, containing moiety Y, in the presence of a phase transfer catalyst;
- wherein X is chloro or bromo;
- R1 is selected from the group consisting of hydrogen and branched and unbranched alkyl and aryl groups having from 1 to 9 carbon atoms;
- Y is selected from the group consisting of —OR2, —NHR2, —NR2R3, —SR2, and —CN;
- and R2 and R3 are independently selected from the group consisting of hydrogen and branched and unbranched alkyl groups having from 1 to 4 carbon atoms.
Dependencies are inferred from the claim text.