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    • 1. 发明申请
    • PROCESS FOR PREPARING SUBSTITUTED BIPHENYLS
    • 制备替代BIPHENYLS的方法
    • US20100256418A1
    • 2010-10-07
    • US12726196
    • 2010-03-17
    • Sebastian Peer SMIDTJochen DietzMichael KeilThomas Grote
    • Sebastian Peer SMIDTJochen DietzMichael KeilThomas Grote
    • C07C205/04
    • C07C201/12C07C209/68C07C211/52C07C205/12
    • A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C-6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R.sup.2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of:3 a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.
    • 制备式I取代的联苯的方法,其中取代基定义如下:X是氟或氯; R1是硝基,氨基或NHR3; R2是氰基,硝基,卤素,C1-C6-烷基,C1-C6-6烯基,C1-C6-炔基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6烷基羰基或苯基; R3是C1-C4-烷基,C1-C4-烯基或C1-C4-炔基; n为1,2或3,其中在n为2或3的情况下,R 2基团也可以不同,其包括使其中Hal为卤素且X和R 1的式II化合物与 在碱存在下和选自以下组中的钯催化剂存在下:a)钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态,b)钯在三芳基膦或三烷基膦存在下的盐 作为络合配体或c)金属钯,任选地在三芳基膦或三烷基膦存在下,在溶剂中与二苯基硼酸(III)反应,其中R 2和n如上所定义,其中使用三芳基膦或三烷基膦 可以被替代。
    • 4. 发明申请
    • Process for Preparing Substituted Biphenyls
    • 制备取代联苯的方法
    • US20090005597A1
    • 2009-01-01
    • US12087345
    • 2007-05-31
    • Sebastian Peer SmidtJochen DietzMichael KeilThomas Grote
    • Sebastian Peer SmidtJochen DietzMichael KeilThomas Grote
    • C07C201/12C07C209/68
    • C07C201/12C07C209/68C07C211/52C07C205/12
    • A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of: a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.
    • 制备式I取代的联苯的方法,其中取代基定义如下:X是氟或氯; R1是硝基,氨基或NHR3; R2是氰基,硝基,卤素,C1-C6-烷基,C1-C6-烯基,C1-C6-炔基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6-烷基羰基或苯基; R3是C1-C4-烷基,C1-C4-烯基或C1-C4-炔基; n为1,2或3,其中在n为2或3的情况下,R2基团也可以不同,其包括使Hal为卤素的化合物与X和R 1如上所定义的化合物反应在 存在碱和钯催化剂,其选自:a)钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态,b)钯在三芳基膦或三烷基膦作为络合配体的存在下的盐,或 c)金属钯,任选地在三芳基膦或三烷基膦存在下,在溶剂中与其中R 2和n如上定义的二苯基硼酸(III)反应,其中所用的三芳基膦或三烷基膦可以被取代。
    • 5. 发明授权
    • Process for preparing substituted biphenyls
    • 制备取代联苯的方法
    • US08030527B2
    • 2011-10-04
    • US12726196
    • 2010-03-17
    • Sebastian Peer SmidtJochen DietzMichael KeilThomas Grote
    • Sebastian Peer SmidtJochen DietzMichael KeilThomas Grote
    • C07C205/06
    • C07C201/12C07C209/68C07C211/52C07C205/12
    • A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C-6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R.sup.2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of:3 a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.
    • 制备式I取代的联苯的方法,其中取代基定义如下:X是氟或氯; R1是硝基,氨基或NHR3; R2是氰基,硝基,卤素,C1-C6-烷基,C1-C6-6烯基,C1-C6-炔基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6-烷基羰基或苯基; R3是C1-C4-烷基,C1-C4-烯基或C1-C4-炔基; n为1,2或3,其中在n为2或3的情况下,R 2基团也可以不同,其包括使其中Hal为卤素且X和R 1的式II化合物与 在碱存在下和选自以下组中的钯催化剂存在下:a)钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态,b)钯在三芳基膦或三烷基膦存在下的盐 作为络合配体或c)金属钯,任选地在三芳基膦或三烷基膦存在下,在溶剂中与二苯基硼酸(III)反应,其中R 2和n如上所定义,其中使用三芳基膦或三烷基膦 可以被替代。
    • 6. 发明授权
    • Process for preparing substituted biphenyls
    • 制备取代联苯的方法
    • US07709684B2
    • 2010-05-04
    • US12087345
    • 2007-05-31
    • Sebastian Peer SmidtJochen DietzMichael KeilThomas Grote
    • Sebastian Peer SmidtJochen DietzMichael KeilThomas Grote
    • C07C211/45C07C211/48C07C205/06
    • C07C201/12C07C209/68C07C211/52C07C205/12
    • A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: X is fluorine or chlorine; R1 is nitro, amino or NHR3; R2 is cyano, nitro, halogen, C1-C6-alkyl, C1-C6-alkenyl, C1-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-alkylcarbonyl or phenyl; R3 is C1-C4-alkyl, C1-C4-alkenyl or C1-C4-alkynyl; n is 1, 2 or 3, where in case that n is 2 or 3, the R2 radicals may also be different, which comprises reacting the compound of the formula II in which Hal is halogen and X and R1 are as defined above, in the presence of a base and of a palladium catalyst selected from the group of: a) palladium-triarylphosphine or -trialkylphosphine complex with palladium in the zero oxidation state, b) salt of palladium in the presence of triarylphospine or trialkylphosphine as a complex ligand or c) metallic palladium, optionally applied to support, in the presence of triarylphosphine or trialkylphosphine, in a solvent, with a diphenylborinic acid (III) in which R2 and n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.
    • 制备式I取代的联苯的方法,其中取代基定义如下:X是氟或氯; R1是硝基,氨基或NHR3; R2是氰基,硝基,卤素,C1-C6-烷基,C1-C6-烯基,C1-C6-炔基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6-烷基羰基或苯基; R3是C1-C4-烷基,C1-C4-烯基或C1-C4-炔基; n为1,2或3,其中在n为2或3的情况下,R2基团也可以不同,其包括使Hal为卤素的化合物与X和R 1如上所定义的化合物反应在 存在碱和钯催化剂,其选自:a)钯 - 三芳基膦或三烷基膦配合物与钯在零氧化状态,b)钯在三芳基膦或三烷基膦作为络合配体存在下的盐,或 c)金属钯,任选地在三芳基膦或三烷基膦存在下,在溶剂中与其中R 2和n如上定义的二苯基硼酸(III)反应,其中所用的三芳基膦或三烷基膦可以被取代。
    • 7. 发明申请
    • Method for Producing Difluoromethyl-Substituted Pyrazole Compounds
    • 二氟甲基取代吡唑化合物的制备方法
    • US20100184994A1
    • 2010-07-22
    • US12664448
    • 2008-06-13
    • Markus NettThomas GroteJan Klaas LohmannJochen DietzSebastian Peer SmidtMichael RackThomas Zierke
    • Markus NettThomas GroteJan Klaas LohmannJochen DietzSebastian Peer SmidtMichael RackThomas Zierke
    • C07D231/14C07C229/06
    • C07D231/12C07D231/14
    • 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.
    • 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。
    • 8. 发明授权
    • Method for producing difluoromethyl-substituted pyrazole compounds
    • 二氟甲基取代的吡唑化合物的制备方法
    • US08188295B2
    • 2012-05-29
    • US12664448
    • 2008-06-13
    • Markus NettThomas GroteJan Klaas LohmannJochen DietzSebastian Peer SmidtMichael RackThomas Zierke
    • Markus NettThomas GroteJan Klaas LohmannJochen DietzSebastian Peer SmidtMichael RackThomas Zierke
    • C07D231/14C07C229/06
    • C07D231/12C07D231/14
    • 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.
    • 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。