公开(公告)号：US08115012B2

公开(公告)日：2012-02-14

申请号：US12513003

申请日：2007-11-02

申请人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

发明人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

IPC分类号： C07D231/10 ,  C07F7/08

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; and R2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than −0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.325 kPa); and b) the reaction mixture from step a) is reacted with a compound of the general formula III R2HN—NH2  (III) in which R2 has one of the meanings given above.

摘要翻译： 本发明涉及制备式Ⅰ的二氟甲基取代的吡唑-4-基羧酸酯的方法，其中R 1是C 1 -C 8烷基，C 3 -C 8环烷基，C 1 -C 4烷氧基-C 1 -C 4烷基等 。 R 2是氢，C 1 -C 4 - 烷基，苄基或苯基，其中a）通式II的化合物，其中X是氟，氯或溴，R 1具有上面给出的含义之一，R 4是C 1 -C 8 - 烷基，C 3 -C 8 - 环烷基，C 2 -C 8 - 烯基，苄基或苯基与通式R 3 n SiCl（4-n）的硅烷化合物反应，其中n为1,2或3，取代基R 3独立地为 选自由C 1 -C 8 - 烷基和苯基组成的组中的一种，以及选自元素周期表第1,2,3,4和12族金属的金属，其氧化还原电位小于-0.7 V，基于正常的氢电极（在25℃和101.325kPa）; 和b）将来自步骤a）的反应混合物与通式III的化合物R2HN-NH2（III）反应，其中R2具有上述含义之一。

公开(公告)号：US20100069646A1

公开(公告)日：2010-03-18

申请号：US12513003

申请日：2007-11-02

申请人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

发明人： Martin Sukopp ,  Michael Rack ,  Sebastian Peer Smidt ,  Sandra Löhr ,  Michael Keil ,  Jochen Dietz ,  Joachim Rheinheimer ,  Thomas Grote ,  Thomas Zierke ,  Jan Klaas Lohmann

IPC分类号： C07D231/10 ,  C07F7/08

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which R1 is C1-C8-alkyl, C3-C8-cycloalkyl, C1-C4-alkoxy-C1-C4-alkyl, etc.; and R2 is hydrogen, C1-C4-alkyl, benzyl or phenyl, wherein a) a compound of the general formula II in which X is fluorine, chlorine or bromine, R1 has one of the meanings given above and R4 is C1-C8-alkyl, C3-C8-cycloalkyl, C2-C8-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula R3nSiCl(4-n) in which n is 1, 2 or 3 and the substituents R3 are independently of one another selected from the group consisting of C1-C8-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than −0.7 V, based on a normal hydrogen electrode (at 25° C. and 101.325 kPa); and b) the reaction mixture from step a) is reacted with a compound of the general formula III R2HN—NH2   (III) in which R2 has one of the meanings given above.

摘要翻译： 本发明涉及制备式Ⅰ的二氟甲基取代的吡唑-4-基羧酸酯的方法，其中R 1是C 1 -C 8烷基，C 3 -C 8环烷基，C 1 -C 4烷氧基-C 1 -C 4烷基等 。 并且R 2是氢，C 1 -C 4 - 烷基，苄基或苯基，其中a）通式II的化合物，其中X是氟，氯或溴，R 1具有上面给出的含义之一，R 4是C 1 -C 8 - 烷基，C 3 -C 8 - 环烷基，C 2 -C 8 - 烯基，苄基或苯基与通式R 3 n SiCl（4-n）的硅烷化合物反应，其中n为1,2或3，取代基R 3独立地为 选自由C 1 -C 8 - 烷基和苯基组成的组中的一种，以及选自元素周期表第1,2,3,4和12族金属的金属，其氧化还原电位小于-0.7 V，基于正常的氢电极（在25℃和101.325kPa）; 和b）将来自步骤a）的反应混合物与通式III的化合物R2HN-NH2（III）反应，其中R2具有上述含义之一。

公开(公告)号：US20100184994A1

公开(公告)日：2010-07-22

申请号：US12664448

申请日：2008-06-13

申请人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

发明人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

IPC分类号： C07D231/14 ,  C07C229/06

CPC分类号： C07D231/12 ,  C07D231/14

摘要： The present invention relates to a process for preparing 3-difluoromethyl-substituted pyrazole compounds of the formula (I) in which R1 is H, halogen, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, phenyl, naphthyl, hetaryl, cyano, —C(═O)—OR1a, —C(═O)—NR1bR1c, —C(═O)—SR1d or —C(═S)—SR1e; R2 is H, C1-C4-alkyl, benzyl or phenyl; R3 is H, halogen, C1-C8-alkoxy, C1-C8-haloalkoxy, C3-C8-cycloalkoxy, C2-C8-alkenyloxy, C1-C8-alkylthio, C1-C8-haloalkylthio, C3-C8-cyclo-alkylthio or C2-C8-alkenylthio; compounds of the formula (II.a) or (II.b), in which R1 and R3 each have one of the definitions given above; R4 is halogen, —OR4a, —SR4a, —O—SO2—R4a or an —NR4bR4c group; R5 and R6 are each C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl, or, together with the nitrogen atom to which they are bonded, are a 3- to 8-membered heterocycle; Lewis acid adducts of compounds of the formula (II.b); the use of compounds of the formula (II.a) or (II.b) and of the Lewis acid adducts for preparing compounds of the formula (I) or (VI); and to a process for converting such compounds to the corresponding 3-difluoro-pyrazol-4-ylcarboxylic acids.

摘要翻译： 本发明涉及制备式（I）的3-二氟甲基取代的吡唑化合物的方法，其中R 1是H，卤素，硝基，C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基， 苯基，萘基，杂芳基，氰基，-C（= O）-OR1a，-C（= O）-NR1bR1c，-C（= O）-SR1d或-C（= S）-SR1e; R2是H，C1-C4-烷基，苄基或苯基; R 3是H，卤素，C 1 -C 8 - 烷氧基，C 1 -C 8 - 卤代烷氧基，C 3 -C 8 - 环烷氧基，C 2 -C 8 - 烯氧基，C 1 -C 8 - 烷硫基，C 1 -C 8 - 卤代烷硫基，C 3 -C 8环 - C 2 -C 8 - 烯硫基; 式（II.a）或（II.b）化合物，其中R 1和R 3各自具有上述定义之一; R4是卤素，-OR4a，-SR4a，-O-SO2-R4a或-NR4bR4c基团; R 5和R 6各自为C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基，苄基或苯基，或与它们所键合的氮原子一起为3-至8-元杂环; 式（II.b）化合物的路易斯酸加合物; 使用式（II.a）或（II.b）化合物和路易斯酸加成物制备式（I）或（VI）化合物的方法; 以及将这些化合物转化为相应的3-二氟 - 吡唑-4-基羧酸的方法。

公开(公告)号：US08188295B2

公开(公告)日：2012-05-29

申请号：US12664448

申请日：2008-06-13

申请人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

发明人： Markus Nett ,  Thomas Grote ,  Jan Klaas Lohmann ,  Jochen Dietz ,  Sebastian Peer Smidt ,  Michael Rack ,  Thomas Zierke

IPC分类号： C07D231/14 ,  C07C229/06

CPC分类号： C07D231/12 ,  C07D231/14

摘要： The present invention relates to a process for preparing 3-difluoromethyl-Substituted pyrazole compounds of the formula (I) in which R1 is H, halogen, nitro, C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, phenyl, naphthyl, hetaryl, cyano, —C(═O)—OR1a, —C(═O)—NR1bR1c, —C(═O)—SR1d or —C(═S)—SR1e; R2 is H, C1-C4-alkyl, benzyl or phenyl; R3 is H, halogen, C1-C8-alkoxy, C1-C8-haloalkoxy, C3-C8-cycloalkoxy, C2-C8-alkenyloxy, C1-C8-alkylthio, C1-C8-haloalkylthio, C3-C8-cyclo-alkylthio or C2-C8-alkenylthio; compounds of the formula (II.a) or (II.b), in which R1 and R3 each have one of the definitions given above; R4 is halogen, —OR4a, —SR4a, —O—SO2—R4a or an —NR4bR4c group; R5 and R6 are each C1-C8-alkyl, C1-C8-haloalkyl, C3-C8-cycloalkyl, benzyl or phenyl, or, together with the nitrogen atom to which they are bonded, are a 3- to 8-membered heterocycle; Lewis acid adducts of compounds of the formula (II.b); the use of compounds of the formula (II.a) or (II.b) and of the Lewis acid adducts for preparing compounds of the formula (I) or (VI); and to a process for converting such compounds to the corresponding 3-difluoro-pyrazol-4-ylcarboxylic acids.

摘要翻译： 本发明涉及一种制备式（I）的3-二氟甲基取代的吡唑化合物的方法，其中R 1是H，卤素，硝基，C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基， 苯基，萘基，杂芳基，氰基，-C（= O）-OR1a，-C（= O）-NR1bR1c，-C（= O）-SR1d或-C（= S）-SR1e; R2是H，C1-C4-烷基，苄基或苯基; R 3是H，卤素，C 1 -C 8 - 烷氧基，C 1 -C 8 - 卤代烷氧基，C 3 -C 8 - 环烷氧基，C 2 -C 8 - 烯氧基，C 1 -C 8 - 烷硫基，C 1 -C 8 - 卤代烷硫基，C 3 -C 8环 - C 2 -C 8 - 烯硫基; 式（II.a）或（II.b）化合物，其中R 1和R 3各自具有上述定义之一; R4是卤素，-OR4a，-SR4a，-O-SO2-R4a或-NR4bR4c基团; R 5和R 6各自为C 1 -C 8 - 烷基，C 1 -C 8 - 卤代烷基，C 3 -C 8 - 环烷基，苄基或苯基，或与它们所键合的氮原子一起为3-至8-元杂环; 式（II.b）化合物的路易斯酸加合物; 使用式（II.a）或（II.b）化合物和路易斯酸加成物制备式（I）或（VI）化合物的方法; 以及将这些化合物转化为相应的3-二氟 - 吡唑-4-基羧酸的方法。

公开(公告)号：US20100174094A1

公开(公告)日：2010-07-08

申请号：US12601966

申请日：2008-05-30

申请人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

发明人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

IPC分类号： C07D231/18 ,  C07D231/12

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R1 is optionally substituted phenyl or C3-C7-cycloalkyl, R1a is hydrogen or fluorine, or R1a together with R1 is optionally substituted C3-C5-alkanediyl or C5-C7-cycloalkanediyl, R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C4-alkoxy-C1-C2-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R1, R1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

摘要翻译： 本发明涉及式（I）的N-取代的（3-二卤代甲基吡唑-4-基）甲酰胺的制备方法，其中R 1为任选取代的苯基或C 3 -C 7 - 环烷基，R 1a为氢或氟，或R 1a R 1是C 1 -C 6 - 烷基，C 2 -C 6 - 烯基，C 2 -C 6炔基或C 1 -C 4 - 烷氧基-C 1 -C 2 - 烷基，其中R 1是任选取代的C 3 -C 5 - 烷二基或C 5 -C 7 - 环烷二基， X是F或Cl，n是0,1,2或3; 其包括A）提供其中X为F或Cl，Y为Cl或Br的式（II）化合物，R 2具有上述含义之一，B）使式（II）化合物与一氧化碳 和其中R1，R1a和n具有上述含义之一的式（III）化合物; 在钯催化剂的存在下; 用于根据本发明的方法制备的中间体，以及其制备方法。

公开(公告)号：US08153820B2

公开(公告)日：2012-04-10

申请号：US12601966

申请日：2008-05-30

申请人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

发明人： Thomas Zierke ,  Joachim Rheinheimer ,  Michael Rack ,  Sebastian Peer Smidt ,  Ansgar Gereon Altenhoff ,  Joachim Schmidt-Leithoff ,  Nina Challand

IPC分类号： C07D231/10

CPC分类号： C07D231/14

摘要： The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which R1 is optionally substituted phenyl or C3-C7-cycloalkyl, R1a is hydrogen or fluorine, or R1a together with R1 is optionally substituted C3-C5-alkanediyl or C5-C7-cycloalkanediyl, R2 is C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or C1-C4-alkoxy-C1-C2-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprises A) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and R2 has one of the meanings given above and B) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R1, R1a and n have one of the meanings given above; in the presence of a palladium catalyst; to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

摘要翻译： 本发明涉及式（I）的N-取代的（3-二卤代甲基吡唑-4-基）甲酰胺的制备方法，其中R 1为任选取代的苯基或C 3 -C 7 - 环烷基，R 1a为氢或氟，或R 1a R 1是C 1 -C 6 - 烷基，C 2 -C 6 - 烯基，C 2 -C 6炔基或C 1 -C 4 - 烷氧基-C 1 -C 2 - 烷基，其中R 1是任选取代的C 3 -C 5 - 烷二基或C 5 -C 7 - 环烷二基， X是F或Cl，n是0,1,2或3; 其包括A）提供其中X为F或Cl，Y为Cl或Br的式（II）化合物，R 2具有上述含义之一，B）使式（II）化合物与一氧化碳 和其中R1，R1a和n具有上述含义之一的式（III）化合物; 在钯催化剂的存在下; 用于根据本发明的方法制备的中间体，以及其制备方法。

公开(公告)号：US20110004002A1

公开(公告)日：2011-01-06

申请号：US12919842

申请日：2009-02-27

申请人： Volker Maywald ,  Sebastian Peer Smidt ,  Bernd Wolf ,  Christopher Koradin ,  Thomas Zierke ,  Michael Rack ,  Michael Keil

发明人： Volker Maywald ,  Sebastian Peer Smidt ,  Bernd Wolf ,  Christopher Koradin ,  Thomas Zierke ,  Michael Rack ,  Michael Keil

IPC分类号： C07D231/14 ,  C07C69/66

CPC分类号： C07D231/14 ,  C07C67/343 ,  C07C69/72

摘要： A process for preparing alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrates (VI) where R is methyl or ethyl, from crude reaction mixtures of alkyl 4,4-difluoroacetoacetates (I) by a) reacting where M is a sodium or potassium ion, and without additional solvent to form an enolate (V) b) releasing the corresponding alkyl 4,4-difluoroacetoacetate (I) from the enolate (V) by means of acid, c) removing the salt formed from cation M and acid anion as a solid and d) converting (I), without isolation from the crude reaction mixture, to the alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrate (VI), and the use of (VI) for preparing 1-methyl-3-difluoromethyl-pyrazol-3-ylcarboxyates VII

摘要翻译： 由烷基4,4-二氟乙酰乙酸酯（I）的粗反应混合物制备R为甲基或乙基的2-烷氧基亚甲基-4,4-二氟-3-氧代丁酸烷基酯（VI）的方法，通过a）使M 钠离子或钾离子，无另外的溶剂以形成烯醇化物（Ⅴ）b）通过酸从烯醇化物（Ⅴ）中释出相应的4,4-二氟乙酰乙酸烷基酯（Ⅰ），c）除去由阳离子M形成的盐 和酸阴离子作为固体，以及d）将（I）从粗反应混合物中分离出来，转化为2-烷氧基亚甲基-4,4-二氟-3-氧代丁酸烷基酯（VI），以及（VI）用于 制备1-甲基-3-二氟甲基 - 吡唑-3-基羧酸酯VII

公开(公告)号：US08350046B2

公开(公告)日：2013-01-08

申请号：US12990892

申请日：2009-05-06

申请人： Wolfgang Reichert ,  Christopher Koradin ,  Sebastian Peer Smidt ,  Volker Maywald ,  Bernd Wolf ,  Michael Rack ,  Thomas Zierke ,  Michael Keil

发明人： Wolfgang Reichert ,  Christopher Koradin ,  Sebastian Peer Smidt ,  Volker Maywald ,  Bernd Wolf ,  Michael Rack ,  Thomas Zierke ,  Michael Keil

IPC分类号： C07D213/82 ,  C07D231/14

CPC分类号： C07C231/02 ,  C07C2601/14 ,  C07D213/82 ,  C07D231/14 ,  C07D231/16 ,  C07C233/65 ,  C07C233/75

摘要： A process for preparing arylcarboxamides of the formula (I) where Ar=a mono- to trisubstituted phenyl, pyridyl or pyrazolyl ring, where the substituents are selected from halogen, C1-C4-alkyl and C1-C4-haloalkyl; M=thienyl or phenyl, which may bear a halogen substituent; Q=direct bond, cyclopropylene, fused bicyclo[2.2.1]heptane or bicyclo[2.2.1]heptene ring; R1=hydrogen, halogen, C1-C6-alkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, mono- to trisubstituted phenyl, where the substituents are selected from halogen and trifluoromethylthio, or cyclopropyl; by reacting an acid chloride of the formula (II) with an arylamine (III) in a suitable nonaqueous solvent, wherein, in the absence of an auxiliary base, a) the acid chloride (II) is initially charged, b) a pressure of from 0 to 700 mbar is established, c) the arylamine (III) is metered in an approximately stoichiometric amount and d) the product of value is isolated.

摘要翻译： 制备式（I）的芳基羧酰胺的方法，其中Ar =单 - 三取代的苯基，吡啶基或吡唑基环，其中取代基选自卤素，C 1 -C 4 - 烷基和C 1 -C 4卤代烷基; M =噻吩基或苯基，其可以带有卤素取代基; Q =直接键合，亚环丙基，稠合双环[2.2.1]庚烷或双环[2.2.1]庚烯环; R1 =氢，卤素，C1-C6-烷基，C1-C4-烷氧基，C1-C4-卤代烷氧基，一至三取代的苯基，其中取代基选自卤素和三氟甲硫基，或环丙基; 通过使式（II）的酰氯与芳基胺（III）在合适的非水溶剂中反应，其中在没有辅助碱的情况下，a）最初加入酰氯（II），b） 建立0至700毫巴，c）芳基胺（III）以约化学计量的量计量，并且d）分离产物的值。

公开(公告)号：US08586750B2

公开(公告)日：2013-11-19

申请号：US12990364

申请日：2009-04-30

申请人： Thomas Zierke ,  Volker Maywald ,  Michael Rack ,  Sebastian Peer Smidt ,  Michael Keil ,  Bernd Wolf ,  Christopher Koradin

发明人： Thomas Zierke ,  Volker Maywald ,  Michael Rack ,  Sebastian Peer Smidt ,  Michael Keil ,  Bernd Wolf ,  Christopher Koradin

IPC分类号： C07D295/145 ,  C07D211/34 ,  C07D265/30

CPC分类号： C07D295/145 ,  C07D231/14

摘要： The present invention relates to a process for preparing 2-(aminomethylidene)-4,4-dihalo-3-oxobutyric esters of the formula (I), wherein R1, R2, R3 are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl, and/or R2 together with R3 and the nitrogen atom to which the two radicals are attached are a heterocyclic radical, in which a corresponding 3-aminoacrylic ester is reacted with a halogen-substituted acetyl fluoride in the presence of at least one alkali or alkaline earth metal fluoride; and the further conversion of halogen-substituted 2-(aminomethylidene)-3-oxobutyric esters of the formula (I) to halomethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.

摘要翻译： 本发明涉及制备式（I）的2-（氨基亚甲基）-4,4-二卤代-3-氧代丁酸酯的方法，其中R1，R2，R3是C1-C6-烷基，C1-C6-卤代烷基 ，C 2 -C 6 - 烯基，C 3 -C 10 - 环烷基或苄基，和/或R 2与R 3和两个基团所连接的氮原子是杂环基团，其中相应的3-氨基丙烯酸酯与 卤素取代的乙酰氟在至少一种碱金属或碱土金属氟化物的存在下; 以及将式（I）的卤素取代的2-（氨基亚甲基）-3-氧代丁酸酯进一步转化为卤代甲基取代的吡唑-4-基羧酸及其酯。

公开(公告)号：US08344157B2

公开(公告)日：2013-01-01

申请号：US13054642

申请日：2009-07-10

申请人： Bernd Wolf ,  Sebastian Peer Smidt ,  Volker Maywald ,  Christopher Koradin ,  Michael Keil ,  Thomas Zierke ,  Michael Rack

发明人： Bernd Wolf ,  Sebastian Peer Smidt ,  Volker Maywald ,  Christopher Koradin ,  Michael Keil ,  Thomas Zierke ,  Michael Rack

IPC分类号： C07D231/10

CPC分类号： C07D233/90

摘要： A process for preparing 1,3-disubstituted pyrazolecarboxylic esters of the formula (I) where X, Y, Z=hydrogen or halogen and R1=C1-C6-alkyl, by metering an enol ether of the formula III where R2 is C1-C6-alkyl at from (−41) to (−80)° C. into an alkyl hydrazine of the formula II H2N—NH-lower alkyl   (II).

摘要翻译： 通过计量式III的烯醇醚制备其中X，Y，Z =氢或R 1 = C 1 -C 6烷基的式（I）的1,3-二取代吡唑羧酸酯的方法，其中R2是C1- （-41）至（-80）℃的C 6 - 烷基转化为式II的烷基肼H 2 NH-NH-低级烷基（II）。