WO2022100195A1 - Procédé de préparation de chlorure de 2-fluoro-5-méthoxybenzènesulfonyle - Google Patents

Procédé de préparation de chlorure de 2-fluoro-5-méthoxybenzènesulfonyle Download PDF

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Publication number
WO2022100195A1
WO2022100195A1 PCT/CN2021/114067 CN2021114067W WO2022100195A1 WO 2022100195 A1 WO2022100195 A1 WO 2022100195A1 CN 2021114067 W CN2021114067 W CN 2021114067W WO 2022100195 A1 WO2022100195 A1 WO 2022100195A1
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WO
WIPO (PCT)
Prior art keywords
fluoro
metal
chloride
methoxybenzenesulfonyl chloride
lithium
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PCT/CN2021/114067
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English (en)
Chinese (zh)
Inventor
张澎涛
徐俊杰
竺伟
Original Assignee
尚科生物医药（上海）有限公司
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Publication of WO2022100195A1 publication Critical patent/WO2022100195A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/87—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton

Definitions

  • the present disclosure belongs to the field of medicinal chemistry, and in particular relates to a method for preparing 2-fluoro-5-methoxybenzenesulfonyl chloride.
  • 2-Fluoro-5-methoxybenzenesulfonyl chloride (CAS number: 1214334-01-6), whose structure is shown in formula I, is an important intermediate for the synthesis of various new drugs.
  • Patent WO2014140065 discloses a new compound, N-(4-(azaindol-6-yl)-phenyl)-sulfonamide, which is a valuable pharmacologically active compound that modulates protein kinase activity, especially Serum and glucocorticoid-regulated kinase (SGK) activity is a potential drug for the treatment of diseases with inappropriate SGK activity, such as degenerative joint diseases or inflammatory processes such as osteoarthritis or rheumatism.
  • SGK Serum and glucocorticoid-regulated kinase
  • Patent WO2015198045 discloses new compounds, 3-substituted 2-aminoindole derivatives and analogs, which are potential drugs for the treatment or prevention of GPR43 receptor-related disorders, such as diabetes, obesity and inflammatory bowel disease.
  • 2-fluoro-5-methoxybenzenesulfonyl chloride is an important raw material for the synthesis of related compounds, and the synthetic route is shown in Scheme 1.
  • the purpose of the present disclosure is to provide a preparation method of 2-fluoro-5-methoxybenzenesulfonyl chloride which is easy to operate and easy to industrialize in view of the deficiencies of the prior art.
  • X is selected from F, Cl, Br and I; M is selected from Mg, Zn, Li and combinations thereof.
  • the operation steps are: using 3-bromo-4-fluoroanisole as raw material, reacting with metal or metal reagent to obtain aryl metal reagent III, and then reacting with sulfonyl chloride to obtain 2-fluoro-5-methoxyl group Benzenesulfonyl chloride.
  • the metal or metal reagent is selected from the group consisting of C 1 -C 6 straight or branched alkyl magnesium, C 1 -C 6 straight or branched alkyl magnesium halide, lithium halide, C 1 -C 6 One or a mixture of linear or branched alkyl lithium, metal magnesium, metal zinc, and metal lithium.
  • the metal or metal reagent is selected from magnesium metal, C1 - C6 straight or branched alkyl magnesium, C1 - C6 straight or branched alkyl magnesium halide lithium halide.
  • the metal reagent is selected from the group consisting of isopropylmagnesium chloride lithium chloride, isopropylmagnesium bromide lithium chloride, isopropylmagnesium chloride, isopropylmagnesium bromide, preferably isopropylmagnesium chloride lithium chloride .
  • the beneficial effect of the present disclosure is that the present disclosure provides a new and unreported preparation method of 2-fluoro-5-methoxybenzenesulfonyl chloride, using 3-bromo-4-fluoroanisole as a raw material,
  • the reaction steps are short, the operation is simple, the reaction conditions are mild, and the method is suitable for industrial production.
  • the tetrahydrofuran was removed by rotary evaporation, extracted with dichloromethane, washed with water, and rotary evaporation was performed to obtain a brown liquid, and oil pump distillation was used to obtain 4.2 g of a colorless liquid.
  • the 1 H NMR chart is shown in FIG. 1 .

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de préparation de chlorure de 2-fluoro-5-méthoxybenzènesulfonyle. Le 3-bromo-4-fluoroanisole est utilisé en tant que matière première et réagit avec un métal ou un réactif métallique pour obtenir un réactif métallique aryle, qui réagit ensuite avec du chlorure de sulfonyle pour obtenir du chlorure de 2-fluoro-5-méthoxybenzènesulfonyle. Le procédé selon la présente invention présente des étapes de réaction courtes, un fonctionnement simple et des conditions de réaction modérées, et est approprié pour une production industrielle.
PCT/CN2021/114067 2020-11-16 2021-08-23 Procédé de préparation de chlorure de 2-fluoro-5-méthoxybenzènesulfonyle WO2022100195A1 (fr)

Applications Claiming Priority (2)

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CN202011278152.XA CN114507163A (zh) 2020-11-16 2020-11-16 一种制备2-氟-5-甲氧基苯磺酰氯的方法
CN202011278152.X 2020-11-16

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WO2022100195A1 true WO2022100195A1 (fr) 2022-05-19

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103012407A (zh) * 2011-09-27 2013-04-03 赛诺菲 N-[4-(1H-吡唑并[3,4-b]吡嗪-6-基)-苯基]-磺酰胺类及其作为药物的用途
CN108003161A (zh) * 2016-10-28 2018-05-08 正大天晴药业集团股份有限公司 神经营养因子酪氨酸激酶受体抑制剂
CN109593803A (zh) * 2018-12-24 2019-04-09 上海健康医学院 (r)-2-(2,5-二氟苯基)吡咯烷或其盐的制备方法
CN109593802A (zh) * 2018-12-24 2019-04-09 上海健康医学院 一种(r)-2-(2,5-二氟苯基)吡咯烷或其盐的制备方法
WO2020079205A1 (fr) * 2018-10-19 2020-04-23 Les Laboratoires Servier Nouveaux dérivés d'amino-pyrimidonyl-pipéridinyl, leur procédé de préparation et compositions pharmaceutiques les contenant
CN111647011A (zh) * 2020-07-16 2020-09-11 宁夏中星显示材料有限公司 一种单卤代苯硼酸的制备方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103012407A (zh) * 2011-09-27 2013-04-03 赛诺菲 N-[4-(1H-吡唑并[3,4-b]吡嗪-6-基)-苯基]-磺酰胺类及其作为药物的用途
CN108003161A (zh) * 2016-10-28 2018-05-08 正大天晴药业集团股份有限公司 神经营养因子酪氨酸激酶受体抑制剂
WO2020079205A1 (fr) * 2018-10-19 2020-04-23 Les Laboratoires Servier Nouveaux dérivés d'amino-pyrimidonyl-pipéridinyl, leur procédé de préparation et compositions pharmaceutiques les contenant
CN109593803A (zh) * 2018-12-24 2019-04-09 上海健康医学院 (r)-2-(2,5-二氟苯基)吡咯烷或其盐的制备方法
CN109593802A (zh) * 2018-12-24 2019-04-09 上海健康医学院 一种(r)-2-(2,5-二氟苯基)吡咯烷或其盐的制备方法
CN111647011A (zh) * 2020-07-16 2020-09-11 宁夏中星显示材料有限公司 一种单卤代苯硼酸的制备方法

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DAVIES ALYN T., CURTO JOHN M., BAGLEY SCOTT W., WILLIS MICHAEL C.: "One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 8, no. 2, 1 January 2017 (2017-01-01), United Kingdom , pages 1233 - 1237, XP055930360, ISSN: 2041-6520, DOI: 10.1039/C6SC03924C *
HAY J. V.: "CHEMISTRY OF SULFONYLUREA HERBICIDES.", PESTICIDE SCIENCE., ELSEVIER APPLIED SCIENCE PUBLISHER. BARKING., GB, vol. 29., no. 03., 1 January 1990 (1990-01-01), GB , pages 247 - 261., XP000202810, ISSN: 0031-613X *
LEO A. PAQUETTE: "Encyclopedia of reagents for organic synthesis; Vol. 7 : Sod - Trim", WILEY , Chichester , ISBN: 978-0-470-84289-8, article ANILKUMAR R., BURTON DONALD J.: "Chloropentafluorobenzene", XP055930355, DOI: 10.1002/047084289X.rn00539 *
MICHAEL A. WALLACE, CONRAD E. RAAB, DENNIS C. DEAN, DAVID G. MELILLO: "Synthesis of [35S]aryl sulfonyl chlorides from [35S]elemental sulfur", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 48, no. 4, 30 March 2005 (2005-03-30), GB , pages 275 - 283, XP055661462, ISSN: 0362-4803, DOI: 10.1002/jlcr.920 *
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