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METHODS OF FORMING 4-CHLORO-2-FLUORO-3-SUBSTITUTED-PHENYLBORONIC ACID PINACOL ESTERS AND METHODS OF USING THE SAME

  • US 20150203514A1
  • Filed: 11/06/2014
  • Published: 07/23/2015
  • Est. Priority Date: 12/30/2011
  • Status: Active Grant
First Claim
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1. A method of forming a 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol ester, comprising:

  • contacting a 1-chloro-3-fluoro-2-substituted benzene with an alkyl lithium to form a lithiated 1-chloro-3-fluoro-2-substituted benzene;

    contacting the lithiated 1-chloro-3-fluoro-2-substituted benzene with an electrophilic boronic acid derivative to form a 4-chloro-2-fluoro-3-substituted-phenylboronate;

    reacting the 4-chloro-2-fluoro-3-substituted-phenylboronate with an aqueous base to form a (4-chloro-2-fluoro-3-substituted-phenyl)trihydroxyborate;

    reacting the (4-chloro-2-fluoro-3-substituted-phenyl)trihydroxyborate with an acid to form a 4-chloro-2-fluoro-3-substituted-phenylboronic acid;

    reacting the 4-chloro-2-fluoro-3-substituted-phenylboronic acid with 2,3-dimethyl-2,3-butanediol to form a 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol ester; and

    subjecting the 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol ester to a Suzuki'"'"'s coupling reaction in a medium consisting essentially of at least one solvent, a Suzuki'"'"'s coupling reactant, a palladium catalyst, a ligand, and a base.

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