AR108531A1 - SYNTHESIS OF 6-ARIL-4-AMYNOPYCHOLINATES AND 2-ARIL-6-AMYNOPIRIMIDIN-4-CARBOXYLATES THROUGH DIRECT SUZUKI COUPLING - Google Patents
SYNTHESIS OF 6-ARIL-4-AMYNOPYCHOLINATES AND 2-ARIL-6-AMYNOPIRIMIDIN-4-CARBOXYLATES THROUGH DIRECT SUZUKI COUPLINGInfo
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- AR108531A1 AR108531A1 ARP170101357A ARP170101357A AR108531A1 AR 108531 A1 AR108531 A1 AR 108531A1 AR P170101357 A ARP170101357 A AR P170101357A AR P170101357 A ARP170101357 A AR P170101357A AR 108531 A1 AR108531 A1 AR 108531A1
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- alkyl
- aryl
- carboxylates
- chloro
- halogen
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
Abstract
En la presente se describen métodos mejorados para la síntesis de 6-aril-4-aminopicolinatos, tales como arilalquilo y 4-amino-3-cloro-6-(4-cloro-2-fluoro-3-metoxifenil)piridina-2-carboxilatos de alquilo y 4-amino-3-cloro-5-fluoro-6-(4-cloro-2-fluoro-3-metoxifenil)piridina-2-carboxilatos de alquilo y arilalquilo. Los métodos mejorados incluyen una etapa de acopamiento Suzuki directo, que elimina las etapas de protección / desprotección en los procesos químicos actuales y, por lo tanto, elimina o reduce las diversas materias primas, equipos y tiempos de ciclo, así como la modificación de otras condiciones de los procesos que incluyen el uso de AP bruta, uso de ABA-diMe, y variación del pH, concentración del catalizador, composición del solvente y/o procedimientos de tratamiento. La presente se amplió para que incluya la síntesis de 2-aril-6-aminopirimidina-4-carboxilatos. Reivindicación 1: Un método para preparar 6-aril-4-aminopicolinatos de la fórmula (1), en la que Q representa hidrógeno o halógeno; R representa hidrógeno, alquilo, arilo o arilalquilo; W representa H, halógeno, alquilo C₁₋₄ o alcoxi C₁₋₃; X representa H; Y representa halógeno, alquilo C₁₋₄ o alcoxi C₁₋₃; y Z representa H, halógeno, alquilo C₁₋₄ o alcoxi C₁₋₃; en el que el método comprende acoplar una aminopiridina (AP) y un ácido fenilborónico (PBA) mediante acoplamiento Suzuki directo en presencia de un catalizador, en el que la concentración del catalizador es igual o menor que alrededor de 3% en relación con el reactivo limitante y el rendimiento del 6-aril-4-aminopicolinato es de al menos alrededor de 60%.Improved methods for the synthesis of 6-aryl-4-aminopicolinates, such as arylalkyl and 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2- are described herein. alkyl carboxylates and 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl) pyridine-2-alkyl and arylalkyl carboxylates. The improved methods include a direct Suzuki coupling stage, which eliminates the protection / deprotection stages in the current chemical processes and, therefore, eliminates or reduces the various raw materials, equipment and cycle times, as well as the modification of other Process conditions that include the use of crude AP, use of ABA-diMe, and pH variation, catalyst concentration, solvent composition and / or treatment procedures. The present was extended to include the synthesis of 2-aryl-6-aminopyrimidine-4-carboxylates. Claim 1: A method of preparing 6-aryl-4-aminopicolinates of the formula (1), wherein Q represents hydrogen or halogen; R represents hydrogen, alkyl, aryl or arylalkyl; W represents H, halogen, C₁₋₄ alkyl or C₁₋₃ alkoxy; X represents H; Y represents halogen, C₁₋₄ alkyl or C₁₋₃ alkoxy; and Z represents H, halogen, C₁₋₄ alkyl or C₁₋₃ alkoxy; wherein the method comprises coupling an aminopyridine (AP) and a phenylboronic acid (PBA) by direct Suzuki coupling in the presence of a catalyst, in which the catalyst concentration is equal to or less than about 3% in relation to the reagent Limiting and yield of 6-aryl-4-aminopicolinate is at least about 60%.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662338562P | 2016-05-19 | 2016-05-19 |
Publications (1)
Publication Number | Publication Date |
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AR108531A1 true AR108531A1 (en) | 2018-08-29 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ARP170101357A AR108531A1 (en) | 2016-05-19 | 2017-05-19 | SYNTHESIS OF 6-ARIL-4-AMYNOPYCHOLINATES AND 2-ARIL-6-AMYNOPIRIMIDIN-4-CARBOXYLATES THROUGH DIRECT SUZUKI COUPLING |
Country Status (1)
Country | Link |
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AR (1) | AR108531A1 (en) |
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2017
- 2017-05-19 AR ARP170101357A patent/AR108531A1/en unknown
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