- Safe, Scalable, Inexpensive, and Mild Nickel-Catalyzed Migita-Like C?S Cross-Couplings in Recyclable Water
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A new approach to C?S couplings is reported that relies on nickel catalysis under mild conditions, enabled by micellar catalysis in recyclable water as the reaction medium. The protocol tolerates a wide range of heteroaromatic halides and thiols, including alkyl and heteroaryl thiols, leading to a variety of thioethers in good isolated yields. The method is scalable, results in low residual metal in the products, and is applicable to syntheses of targets in the pharmaceutical area. The procedure also features an associated low E Factor, suggesting a far more attractive entry than is otherwise currently available, especially those based on unsustainable loadings of Pd catalysts.
- Yu, Tzu-Yu,Pang, Haobo,Cao, Yilin,Gallou, Fabrice,Lipshutz, Bruce H.
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supporting information
p. 3708 - 3713
(2020/12/17)
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- PROCESS FOR PREPARING AXITINIB, PROCESS FOR PURIFYING THE INTERMEDIATE 2-((3-IODO-1H-INDAZOL-6-YL)THIO)-N-METHYLBENZAMIDE, PROCESS FOR PURIFYING AXITINIB VIA THE AXITINIB HCL SALT, SOLID FORM OF THE AXITINIB HCL SALT
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1) A process for preparing Axitinib ( N-methyl-2-({3-[(E)-2-pyridin-2- ylethenyl]-lH-indazol-6-yl}sulfanyl)benzamide; compound of formula (l)) 2) A process for purifying the intermediate 2-((3-iodo-lH-indazol-6- yl)thio)-N-methylbenzamide (compound of formula (lla)) 3) A process for purifying Axitinib using the Axitinib HCI salt (compound of formula (VIII)) as an intermediate 4) A solid form of the Axitinib HCI salt (form J) characterized by an XRPD pattern
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Page/Page column 23-24
(2020/10/28)
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- ALKYNYL INDAZOLE DERIVATIVE AND USE THEREOF
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The main object of the present invention is to provide a novel compound which has a VEGF receptor tyrosine kinase inhibitory activity and is useful as an active ingredient for the treatment of diseases accompanying angiogenesis or edema, for example, age-related macular degeneration or the like. The present invention includes, for example, an alkynyl indazole derivative represented by the following general formula (I), a pharmaceutical acceptable salt thereof, and a medicine containing thereof.
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Paragraph 0254; 0255
(2017/02/24)
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- A novel D-glucosamine-derived pyridyltriazole@ palladium catalyst for solvent-free Mizoroki-Heck reactions and its application in the synthesis of Axitinib
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A green method for the synthesis of a D-glucosamine-derived triazole@ palladium catalyst is described. The synthesized catalyst containing a 2-pyridyl-1,2,3-triazole ligand was prepared via a click route in high yields and was explored in Heck cross-coupling reactions between different aryl halides and olefins under solventfree conditions. The catalyst can be separated from the reaction mixture and reused at least six times with superior activity. In addition, using this protocol, the marketed drug Axitinib (antitumor) could be synthesized easily.
- Shen, Chao,Shen, Hongyun,Yang, Ming,Xia, Chengcai,Zhang, Pengfei
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p. 225 - 230
(2018/04/16)
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- Development of an efficient Pd-catalyzed coupling process for axitinib
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The manufacturing process of axitinib (1) involves two Pd-catalyzed coupling reactions, a Migita coupling and a Heck reaction. Optimization of both of these pivotal bond-formation steps is discussed as well as the approach to control impurities in axitinib. Essential to the control strategy was the optimization of the Heck reaction to minimize formation of impurities, in addition to the development of an efficient isolation of crude axitinib to purge impurities.
- Chekal, Brian P.,Guinness, Steven M.,Lillie, Brett M.,McLaughlin, Robert W.,Palmer, Charles W.,Post, Ronald J.,Sieser, Janice E.,Singer, Robert A.,Sluggett, Gregory W.,Vaidyanathan, Rajappa,Withbroe, Gregory J.
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p. 266 - 274
(2014/05/20)
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- Methods of preparing indazole compounds
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The present invention relates to methods for preparing indazole compounds of formula I, which are useful as modulators and/or inhibitors of protein kinases. The present invention also relates to intermediate compounds useful in the preparation of compounds of formula I.
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Page/Page column 36-37
(2010/04/24)
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- Methods of preparing indazole compounds
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The present invention relates to methods for preparing indazole compounds of formula I, which are useful as modulators and/or inhibitors of protein kinases. The present invention also relates to intermediate compounds useful in the preparation of compounds of formula I.
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Page/Page column 26; 27
(2010/11/08)
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- METHODS FOR PREPARING INDAZOLE COMPOUNDS
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The invention relates to methods for preparing indalzole compounds having formula (I) or pharmaceutically acceptable salts or solvates thereof. Compounds of the formula (I) are useful as anti-angiogenesis agents and as agents for modulating and/or inhibiting the activity of protein kinases, thus providing treatments for cancer or other diseases associated with cellular proliferation mediated by protein kinases.
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Page/Page column 28-29
(2008/06/13)
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