Patents by Inventor Jossian Oppenheimer
Jossian Oppenheimer has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 11390587Abstract: Improved methods for preparing chemical precursors to sulfonyl chloride III, which are important intermediates in the preparation of pyroxsulam herbicide are provided. Specifically, these precursors are compounds of Formulas VII and/or VIII, and IX, wherein R is a C1-C6 alkyl, R1 is a C1-C6 alkyl, X is Cl or OH, Y is halogen, OH, or OR2, and R2 is a C1-C6 alkyl.Type: GrantFiled: December 20, 2019Date of Patent: July 19, 2022Assignee: Corteva Agriscience LLCInventors: Jossian Oppenheimer, Matthias S. Ober, Mark E. Ondari, Michael Gullo, Jayachandran Devaraj, Amaruka Hazari, Will Kruper
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Publication number: 20220041554Abstract: Improved methods for preparing chemical precursors to sulfonyl chloride III, which are important intermediates in the preparation of pyroxsulam herbicide are provided. Specifically, these precursors are compounds of Formulas VII and/or VIII, and IX, wherein R is a C1-C6 alkyl, R1 is a C1-C6 alkyl, X is Cl or OH, Y is halogen, OH, or OR2, and R2 is a C1-C6 alkyl.Type: ApplicationFiled: December 20, 2019Publication date: February 10, 2022Applicant: Corteva Agriscience LLCInventors: Jossian Oppenheimer, Matthias S. Ober, Mark E. Ondari, Michael Gullo, Jayachandran Devaraj, Amaruka Hazari, Will Kruper
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Publication number: 20220024873Abstract: Improved methods for preparing chemical precursors to sulfonyl chloride III, which are important intermediates in the preparation of pyroxsulam herbicide, are provided. Also provided are compounds of Formula III, Formula VII, and IV, wherein R1 is a C1-C6 alkyl, X is Cl or OH, Y is halogen, OH, or OR2, and R2 is a C1-C6 alkyl.Type: ApplicationFiled: December 20, 2019Publication date: January 27, 2022Applicant: Geneva Agriscience LLCInventors: Jossian Oppenheimer, Matthias S. Ober, Mark E. Ondari
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Publication number: 20210198262Abstract: The present disclosure concerns a method for preparing florasulam which involves treating a solution of 2,6-difluoroaniline in 1,2-propylene glycol with: a) sulfonyl chloride III and then b) a base to provide, after workup and isolation, florasulam (I) in yields of about 65-85%. The treatment of 2,6-difluoroaniline with sulfonyl chloride III and the base are conducted by controlled additions.Type: ApplicationFiled: October 10, 2018Publication date: July 1, 2021Applicant: Dow AgroSciences LLCInventors: Jossian Oppenheimer, Michael Gullo, David E. Podhorez, Justin A. Alberts
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Patent number: 10570114Abstract: Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.Type: GrantFiled: July 26, 2018Date of Patent: February 25, 2020Assignee: Dow AgroSciences LLCInventors: Jason S. Fisk, Xiaoyong Li, Mark Muehlfeld, Robert S. Bauman, Jossian Oppenheimer, Siyu Tu, Mark A. Nitz, Reetam Chakrabarti, Shawn D. Feist, James W. Ringer, Ronald B. Leng
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Patent number: 10544121Abstract: Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.Type: GrantFiled: July 26, 2018Date of Patent: January 28, 2020Assignee: Dow AgroSciences LLCInventors: Jason S. Fisk, Xiaoyong Li, Mark Muehlfeld, Robert S. Bauman, Jossian Oppenheimer, Siyu Tu, Mark A. Nitz, Reetam Chakrabarti, Shawn D. Feist, James W. Ringer, Ronald B. Leng
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Publication number: 20190106428Abstract: The present disclosure concerns a method for preparing florasulam which involves treating a solution of 2,6-difluoroaniline in 1,2-propylene glycol with: a) sulfonyl chloride III and then b) a base to provide, after workup and isolation, florasulam (I) in yields of about 65-85%. The treatment of 2,6-difluoroaniline with sulfonyl chloride III and the base are conducted by controlled additions.Type: ApplicationFiled: October 10, 2018Publication date: April 11, 2019Applicant: Dow AgroSciences LLCInventors: Jossian Oppenheimer, Michael Gullo, David E. Podhorez, Justin A. Alberts
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Publication number: 20190062350Abstract: Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectively prepare borylated arenes without the need for expensive cryogenic reaction conditions.Type: ApplicationFiled: October 26, 2018Publication date: February 28, 2019Inventors: Milton R. Smith, Robert E. Maleczka, Hao Li, Chathurika R.K. Jayasundara, Jossian Oppenheimer, Dmitrijs Sabasovs
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Patent number: 10166533Abstract: Methods for the borylation of aromatic compounds using cobalt catalysts are provided.Type: GrantFiled: June 16, 2015Date of Patent: January 1, 2019Assignees: Dow AgroSciences LLC, The Board of Regents of the University of MichiganInventors: Milton R. Smith, Robert E. Maleczka, Dmitrijs Sabasovs, Jossian Oppenheimer
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Publication number: 20180334445Abstract: Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This includes synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.Type: ApplicationFiled: July 26, 2018Publication date: November 22, 2018Applicant: Dow AgroSciences LLCInventors: Jason S. F, Xiaoyong Li, Mark Muehlfeld, Robert S. Bauman, Jossian Oppenheimer, Siyu Tu, Mark A. Nitz, Reetam Chakrabarti, Shawn D. Feist, James W. Ringer, Ronald B. Leng
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Patent number: 10125082Abstract: The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.Type: GrantFiled: October 8, 2015Date of Patent: November 13, 2018Assignee: Dow Global Technologies LLCInventors: Patrick S. Hanley, Jossian Oppenheimer, Matthias S. Ober, William J. Kruper, Jr., Arkady L. Krasovskiy
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Patent number: 10112960Abstract: Methods for the selective borylation of arenes, including arenes substituted with an electron-withdrawing group (e.g., 1-chloro-3-fluoro-2-substituted benzenes) are provided. The methods can be used, in some embodiments, to efficiently and regioselectively prepare borylated arenes without the need for expensive cryogenic reaction conditions.Type: GrantFiled: September 5, 2014Date of Patent: October 30, 2018Assignees: Dow AgroSciences LLC, The Board of Regents of the Michigan State UniversityInventors: Milton R. Smith, Robert E. Maleczka, Hao Li, Chathurika R. K. Jayasundara, Jossian Oppenheimer, Dmitrijs Sabasovs
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Patent number: 10087164Abstract: Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalkyl and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This invention was expanded to include synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.Type: GrantFiled: May 19, 2017Date of Patent: October 2, 2018Assignee: Dow AgroSciences LLCInventors: Jason S. Fisk, Xiaoyong Li, Mark Muehlfeld, Robert S. Bauman, Jossian Oppenheimer, Siyu Tu, Mark A. Nitz, Reetam Chakrabarti, Shawn D. Feist, James W. Ringer, Ronald B. Leng
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Publication number: 20170334878Abstract: Improved methods of synthesizing 6-aryl-4-aminopicolinates, such as arylalky and alkyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates and arylalkyl and alkyl 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylates, are described herein. The improved methods include a direct Suzuki coupling step, which eliminates the protection/de-protection steps in the current chemical process, and therefore eliminates or reduces various raw materials, equipment and cycle time as well as modification of other process conditions including use of crude AP, use of ABA-diMe, and varying pH, catalyst concentration, solvent composition, and/or workup procedures. This invention was expanded to include synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates.Type: ApplicationFiled: May 19, 2017Publication date: November 23, 2017Applicant: Dow AgroSciences LLCInventors: Jason S. Fisk, Xiaoyong Li, Mark Muehlfeld, Robert S. Bauman, Jossian Oppenheimer, Siyu Tu, Mark A. Nitz, Reetam Chakrabarti, Shawn D. Feist, James W. Ringer, Ronald B. Leng
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Publication number: 20170240499Abstract: The present disclosure describes a method of coupling a first compound to a second compound, the method comprising: providing the first compound having a fluorosulfonate substituent; providing the second compound comprising an alkene; and reacting the first compound and the second compound in a reaction mixture, the reaction mixture including a catalyst having at least one group 10 atom, the reaction mixture under conditions effective to couple the first compound to the second compound.Type: ApplicationFiled: October 8, 2015Publication date: August 24, 2017Inventors: Patrick S. Hanley, Jossian Oppenheimer, Matthias S. Ober, William J. Kruper, Jr., Arkady L. Krasovskiy
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Patent number: 9422313Abstract: Methods include formation of 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters. The method comprises contacting a 1-chloro-3-fluoro-2-substituted benzene with an alkyl lithium to form a lithiated 1-chloro-3-fluoro-2-substituted benzene. The lithiated 1-chloro-3-fluoro-2-substituted benzene is contacted with an electrophilic boronic acid derivative to form a 4-chloro-2-fluoro-3-substituted-phenylboronate. The 4-chloro-2-fluoro-3-substituted-phenylboronate is reacted with an aqueous base to form a (4-chloro-2-fluoro-3-substituted-phenyl)trihydroxyborate. The (4-chloro-2-fluoro-3-substituted-phenyl)trihydroxyborate is reacted with an acid to form a 4 chloro-2-fluoro-3-substituted-phenylboronic acid. The 4-chloro-2-fluoro-3-substituted-phenylboronic acid is reacted with 2,3-dimethyl-2,3-butanediol to form 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters .Type: GrantFiled: November 6, 2014Date of Patent: August 23, 2016Assignee: Dow AgroSciences LLCInventor: Jossian Oppenheimer
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Methods of isolating (4-chloro-2-fluoro-3-substituted-phenyl)boronates and methods of using the same
Patent number: 9376390Abstract: Methods of isolating a 4-chloro-2-fluoro-3-substituted-phenylboronate include adding carbon dioxide gas or carbon dioxide solid (dry ice) to a solution comprising a 4-chloro-2-fluoro-3-substituted-phenylboronate, an inert organic solvent, and at least one lithium salt to react the at least one lithium salt with the carbon dioxide gas or carbon dioxide solid (dry ice) and form a mixture comprising the 4-chloro-2-fluoro-3-substituted-phenylboronate, the inert organic solvent, and a precipitated solid. The precipitated solid may be removed from the mixture. Methods of using 4-chloro-2-fluoro-3-substituted-phenylboronates to produce methyl-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-substituted-phenyl)pyridine-2-carboxylates are also disclosed.Type: GrantFiled: May 13, 2015Date of Patent: June 28, 2016Assignee: Dow AgroSciences LLCInventors: Jossian Oppenheimer, Catherine A. Menning, Daniel Randolph Henton -
Publication number: 20150361109Abstract: Methods for the borylation of aromatic compounds using cobalt catalysts are provided.Type: ApplicationFiled: June 16, 2015Publication date: December 17, 2015Inventors: Milton R. Smith, Robert E. Maleczka, Dmitrijs Sabasovs, Jossian Oppenheimer
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METHODS OF ISOLATING (4-CHLORO-2-FLUORO-3-SUBSTITUTED-PHENYL)BORONATES AND METHODS OF USING THE SAME
Publication number: 20150239843Abstract: Methods of isolating a 4-chloro-2-fluoro-3-substituted-phenylboronate include adding carbon dioxide gas or carbon dioxide solid (dry ice) to a solution comprising a 4-chloro-2-fluoro-3-substituted-phenylboronate, an inert organic solvent, and at least one lithium salt to react the at least one lithium salt with the carbon dioxide gas or carbon dioxide solid (dry ice) and form a mixture comprising the 4-chloro-2-fluoro-3-substituted-phenylboronate, the inert organic solvent, and a precipitated solid. The precipitated solid may be removed from the mixture. Methods of using 4-chloro-2-fluoro-3-substituted-phenylboronates to produce methyl-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-substituted-phenyl)pyridine-2-carboxylates are also disclosed.Type: ApplicationFiled: May 13, 2015Publication date: August 27, 2015Inventors: Jossian Oppenheimer, Catherine A. Menning, Daniel Randolph Henton -
Publication number: 20150203514Abstract: Methods include formation of 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters. The method comprises contacting a 1-chloro-3-fluoro-2-substituted benzene with an alkyl lithium to form a lithiated 1-chloro-3-fluoro-2-substituted benzene. The lithiated 1-chloro-3-fluoro-2-substituted benzene is contacted with an electrophilic boronic acid derivative to form a 4-chloro-2-fluoro-3-substituted-phenylboronate. The 4-chloro-2-fluoro-3-substituted-phenylboronate is reacted with an aqueous base to form a (4-chloro-2-fluoro-3-substituted-phenyl)trihydroxyborate. The (4-chloro-2-fluoro-3-substituted-phenyl)trihydroxyborate is reacted with an acid to form a 4 chloro-2-fluoro-3-substituted-phenylboronic acid. The 4-chloro-2-fluoro-3-substituted-phenylboronic acid is reacted with 2,3-dimethyl-2,3-butanediol to form 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters .Type: ApplicationFiled: November 6, 2014Publication date: July 23, 2015Inventor: Jossian Oppenheimer