Improved Synthesis of 6-Chloro-5-methylpyridin-2-amine: A Key Intermediate for Making Lumacaftor

doi:10.1021/acs.oprd.9b00556

	Improved Synthesis of 6-Chloro-5-methylpyridin-2-amine: A Key Intermediate for Making Lumacaftor
	Zhang, Junchi 1,2; Zhu, Fuqiang 3; Tian, Guanghui 3; Jiang, Xiangrui 1,2; Shen, Jingshan 1,2
刊名	ORGANIC PROCESS RESEARCH & DEVELOPMENT
	2020-06-19
卷号	24 期号:6 页码:1175-1179
关键词	6-chloro-5-methylpyridin-2-amine lumacaftor methylation safe
ISSN号	1083-6160
DOI	10.1021/acs.oprd.9b00556
通讯作者	Jiang, Xiangrui(jiangxiangrui@simm.ac.cn)
英文摘要	A safe and efficient synthesis of 6-chloro-5-methylpyridin-2-amine, a key intermediate for lumacaftor, is described, which avoids the utilization of peroxide. In this four-step sequence, starting from 2-amino-6-chloropyridine, the crucial 5-position methylation was achieved via a Suzuki-Miyaura cross-coupling reaction. By adopting this synthetic route, 6-chloro-5-methylpyridin-2-amine was produced on a hectogram scale with 62.4% overall yield and 99.49% purity.
资助项目	Special Foundation of the Chinese Academy of Sciences for strategic pilot technology[XDA12050411] ; Special Foundation of the Chinese Academy of Sciences for strategic pilot technology[XDA12040327]
WOS关键词	CYSTIC-FIBROSIS PATIENTS
WOS研究方向	Chemistry
语种	英语
出版者	AMER CHEMICAL SOC
WOS记录号	WOS:000543672300028
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/291752]
专题	中国科学院上海药物研究所
通讯作者	Jiang, Xiangrui
作者单位	1.Univ Chinese Acad Sci, Beijing 100049, Peoples R China 2.Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China 3.Topharman Shanghai Co Ltd, Shanghai 201203, Peoples R China
推荐引用方式 GB/T 7714	Zhang, Junchi,Zhu, Fuqiang,Tian, Guanghui,et al. Improved Synthesis of 6-Chloro-5-methylpyridin-2-amine: A Key Intermediate for Making Lumacaftor[J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT,2020,24(6):1175-1179.
APA	Zhang, Junchi,Zhu, Fuqiang,Tian, Guanghui,Jiang, Xiangrui,&Shen, Jingshan.(2020).Improved Synthesis of 6-Chloro-5-methylpyridin-2-amine: A Key Intermediate for Making Lumacaftor.ORGANIC PROCESS RESEARCH & DEVELOPMENT,24(6),1175-1179.
MLA	Zhang, Junchi,et al."Improved Synthesis of 6-Chloro-5-methylpyridin-2-amine: A Key Intermediate for Making Lumacaftor".ORGANIC PROCESS RESEARCH & DEVELOPMENT 24.6(2020):1175-1179.