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Optimized Synthesis of the Key Intermediate of Telmisartan via the Cyclization of 2-Bromoarylamine with n-Butyronitrile

文献类型：期刊论文

作者Qin, Hongjian2,4; Mintah Bonku, Emmanuel3,4; Odilov, Abdullajon3,4; Wu, Mingjun1; Liu, Yongjian1; Shen, Jingshan3,4; Zhu, Fuqiang1; Aisa, Haji A.2,4
刊名ORGANIC PROCESS RESEARCH & DEVELOPMENT
出版日期2023-11-06
卷号27期号:11页码:2165-2173
ISSN号1083-6160
关键词bis-benzimidazole cyclization 2-bromoarylamine n-butyronitrile telmisartan design of experiments
DOI10.1021/acs.oprd.3c00298
通讯作者Zhu, Fuqiang(fuqiang.zhu@topharman.com) ; Aisa, Haji A.(haji@ms.xjb.ac.cn)
英文摘要Herein, a facile and sustainable synthesis method of bis-benzimidazole compound 5, which is the key intermediate of telmisartan, is realized using commercially available 3-methyl-4-nitrobenzoic acid and 2-chloronitrobenzene as starting materials. Aniline 10 was produced in 98% isolated yield using a one-pot reduction/cyclization procedure. Subsequently, 2-bromoarylamine 11 was prepared in 96% isolated yield via the bromination of aniline 10 with bromine. Finally, bis-benzimidazole 5 synthesis was completed via the cyclization of 2-bromoarylamine 11 with n-butyronitrile; the isolated yield of bis-benzimidazole 5 was 95%, and its high-performance liquid chromatography purity based on area was 99.8%. Each reaction step was optimized to achieve high yields, and the optimal conditions were identified in the final step via the design of experiments. The developed process provides an alternative sustainable route for synthesizing bis-benzimidazole 5; this route avoids undesired nitration using nitric/sulfuric acid and cyclization in polyphosphoric acid, which are used in the current methods.
WOS关键词2-IODOANILINES ; BENZIMIDAZOLES ; EFFICIENT ; HALOGENATION ; BROMINATION ; CONVENIENT
资助项目West Light Foundation, Chinese Academy of Sciences[2018-XBYJRC-001] ; West Light Foundation, Chinese Academy of Sciences[ANSO-CR-SP-2020-03] ; West Light Foundation of the Chinese Academy of Sciences
WOS研究方向Chemistry
语种英语
出版者AMER CHEMICAL SOC
WOS记录号WOS:001141154200001
源URL[http://119.78.100.183/handle/2S10ELR8/308669]  
专题中国科学院上海药物研究所
通讯作者Zhu, Fuqiang; Aisa, Haji A.
作者单位1.Topharman Shanghai Co Ltd, Shanghai 201203, Peoples R China
2.Chinese Acad Sci, Xinjiang Tech Inst Phys & Chem, State Key Lab Basis Xinjiang Indigenous Med Plants, Urumqi 830011, Xinjiang, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
推荐引用方式
GB/T 7714		 Qin, Hongjian,Mintah Bonku, Emmanuel,Odilov, Abdullajon,et al. Optimized Synthesis of the Key Intermediate of Telmisartan via the Cyclization of 2-Bromoarylamine with n-Butyronitrile[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT,2023,27(11):2165-2173.
APA Qin, Hongjian.,Mintah Bonku, Emmanuel.,Odilov, Abdullajon.,Wu, Mingjun.,Liu, Yongjian.,...&Aisa, Haji A..(2023).Optimized Synthesis of the Key Intermediate of Telmisartan via the Cyclization of 2-Bromoarylamine with n-Butyronitrile.ORGANIC PROCESS RESEARCH & DEVELOPMENT,27(11),2165-2173.
MLA Qin, Hongjian,et al."Optimized Synthesis of the Key Intermediate of Telmisartan via the Cyclization of 2-Bromoarylamine with n-Butyronitrile".ORGANIC PROCESS RESEARCH & DEVELOPMENT 27.11(2023):2165-2173.

入库方式： OAI收割

来源：上海药物研究所

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