Methods of forming 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters and methods of using the same
    3.
    发明授权
    Methods of forming 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters and methods of using the same 有权
    形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯的方法及其使用方法

    公开(公告)号:US09422313B2

    公开(公告)日:2016-08-23

    申请号:US14535096

    申请日:2014-11-06

    摘要: 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 . Methods of using 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters to produce 6-(4-chloro-2-fluoro-3-substituted-phenyl)-4-aminopicolinates are also disclosed.

    摘要翻译: 方法包括形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯。 该方法包括使1-氯-3-氟-2-取代的苯与烷基锂接触以形成锂化的1-氯-3-氟-2-取代的苯。 将锂化的1-氯-3-氟-2-取代的苯与亲电子硼酸衍生物接触以形成4-氯-2-氟-3-取代的苯基硼酸酯。 使4-氯-2-氟-3-取代的苯基硼酸酯与水性碱反应形成(4-氯-2-氟-3-取代 - 苯基)三羟基硼酸酯。 (4-氯-2-氟-3-取代 - 苯基)三羟基硼酸酯与酸反应形成4-氯-2-氟-3-取代的苯基硼酸。 4-氯-2-氟-3-取代的苯基硼酸与2,3-二甲基-2,3-丁二醇反应形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯。 还公开了使用4-氯-2-氟-3-取代的苯基硼酸频哪醇酯制备6-(4-氯-2-氟-3-取代的苯基)-4-氨基吡啶酸酯的方法。

    Methods of forming 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters and methods of using the same
    9.
    发明授权
    Methods of forming 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters and methods of using the same 有权
    形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯的方法及其使用方法

    公开(公告)号:US08912339B2

    公开(公告)日:2014-12-16

    申请号:US13722471

    申请日:2012-12-20

    摘要: 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. Methods of using 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters to produce 6-(4-chloro-2-fluoro-3-substituted-phenyl)-4-aminopicolinates are also disclosed.

    摘要翻译: 方法包括形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯。 该方法包括使1-氯-3-氟-2-取代的苯与烷基锂接触以形成锂化的1-氯-3-氟-2-取代的苯。 将锂化的1-氯-3-氟-2-取代的苯与亲电子硼酸衍生物接触以形成4-氯-2-氟-3-取代的苯基硼酸酯。 使4-氯-2-氟-3-取代的苯基硼酸酯与水性碱反应形成(4-氯-2-氟-3-取代 - 苯基)三羟基硼酸酯。 (4-氯-2-氟-3-取代 - 苯基)三羟基硼酸酯与酸反应形成4-氯-2-氟-3-取代的苯基硼酸。 4-氯-2-氟-3-取代的苯基硼酸与2,3-二甲基-2,3-丁二醇反应形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯。 还公开了使用4-氯-2-氟-3-取代的苯基硼酸频哪醇酯制备6-(4-氯-2-氟-3-取代的苯基)-4-氨基吡啶酸酯的方法。

    METHODS OF FORMING 4-CHLORO-2-FLUORO-3-SUBSTITUTED-PHENYLBORONIC ACID PINACOL ESTERS AND METHODS OF USING THE SAME
    10.
    发明申请
    METHODS OF FORMING 4-CHLORO-2-FLUORO-3-SUBSTITUTED-PHENYLBORONIC ACID PINACOL ESTERS AND METHODS OF USING THE SAME 有权
    形成4-氯-2-氟-3-取代 - 苯基硼酸酯的方法及其使用方法

    公开(公告)号:US20130172565A1

    公开(公告)日:2013-07-04

    申请号:US13722471

    申请日:2012-12-20

    IPC分类号: C07F5/04 C07D213/807

    摘要: 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. Methods of using 4-chloro-2-fluoro-3-substituted-phenylboronic acid pinacol esters to produce 6-(4-chloro-2-fluoro-3-substituted-phenyl)-4-aminopicolinates are also disclosed.

    摘要翻译: 方法包括形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯。 该方法包括使1-氯-3-氟-2-取代的苯与烷基锂接触以形成锂化的1-氯-3-氟-2-取代的苯。 将锂化的1-氯-3-氟-2-取代的苯与亲电子硼酸衍生物接触以形成4-氯-2-氟-3-取代的苯基硼酸酯。 使4-氯-2-氟-3-取代的苯基硼酸酯与水性碱反应形成(4-氯-2-氟-3-取代 - 苯基)三羟基硼酸酯。 (4-氯-2-氟-3-取代 - 苯基)三羟基硼酸酯与酸反应形成4-氯-2-氟-3-取代的苯基硼酸。 4-氯-2-氟-3-取代的苯基硼酸与2,3-二甲基-2,3-丁二醇反应形成4-氯-2-氟-3-取代的苯基硼酸频哪醇酯。 还公开了使用4-氯-2-氟-3-取代的苯基硼酸频哪醇酯制备6-(4-氯-2-氟-3-取代的苯基)-4-氨基吡啶酸酯的方法。