Development of an NH4Cl-Catalyzed Ethoxy Ethyl Deprotection in Flow for the Synthesis of Merestinib
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- 作者：Michael O. Frederick ; Joel R. Calvin ; Richard F. Cope ; Michael E. LeTourneau ; Kurt T. Lorenz ; Martin D. Johnson ; Todd D. Maloney ; Yangwei John Pu ; Richard D. Miller ; Lauren E. Cziesla
- 刊名：Organic Process Research & Development
- 出版年：2015
- 出版时间：October 16, 2015
- 年：2015
- 卷：19
- 期：10
- 页码：1411-1417
- 全文大小：328K
- ISSN：1520-586X
文摘
An NH4Cl-catalyzed ethoxy ethyl deprotection was developed for the synthesis of merestinib, a MET inhibitor. Alternative reactor technologies using temperatures above the solvent boiling point are combined with this mild catalyst to promote the deprotection reaction. The reaction is optimized for flow and has been used to synthesize over 100 kg of the target compound. The generality of the reaction conditions is also demonstrated with other compounds and protecting groups.