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ChemicalBook CAS DataBase List Pamiparib
1446261-44-4

Pamiparib synthesis

10synthesis methods
Using 2-bromo-5-fluorobenzoic acid (27.1) as the raw material, a series of reactions were performed to obtain methyl benzoate 27.2, which was then reduced and protected to obtain the key aromatic bromide fragment 27.3. Using pyrrolene 27.4 as the raw material, alkane 27.8 was obtained by reaction with tert-butyl bromoacetate 27.5, addition of acetylene group, removal of silicon group, etc., and then enantiomer separation was performed to obtain the desired (R)-enantiomer 27.10. The alkynyl group 27.10 and the bromide group 27.3 were subjected to Larock heterocyclization reaction to generate indole 27.11, which was then treated with trifluoromethanesulfonic acid and hydrazine hydrate reaction to finally obtain Pamiparib (27) as a semihydrate crystalline solid with a yield of 50%.
Pamiparib
-

Yield:-

Steps:

Multi-step reaction with 12 steps
1.1: chloroform / 6 h / Reflux
2.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 1.5 h / -78 °C / Inert atmosphere
3.1: thionyl chloride / methanol / 1 h / 0 °C
4.1: sodium carbonate / tetrahydrofuran / 0 - 20 °C
5.1: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 °C / Inert atmosphere
6.1: potassium carbonate / methanol / 0 - 20 °C
7.1: N,N,N',N'-tetramethylguanidine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
8.1: zinc dibromide / toluene / 15 h / 80 °C
9.1: sodium tetrahydroborate / methanol / 4 h / Reflux; Inert atmosphere
10.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 20 h / 20 °C
11.1: methanesulfonic acid / 1 h / 60 °C
12.1: acetic acid; hydrazine hydrate / methanol / 5 h / Reflux

References:

Wang, Hexiang;Ren, Bo;Liu, Ye;Jiang, Beibei;Guo, Yin;Wei, Min;Luo, Lusong;Kuang, Xianzhao;Qiu, Ming;Lv, Lei;Xu, Hong;Qi, Ruipeng;Yan, Huibin;Xu, Dexu;Wang, Zhiwei;Huo, Chang-Xin;Zhu, Yutong;Zhao, Yuan;Wu, Yiyuan;Qin, Zhen;Su, Dan;Tang, Tristin;Wang, Fan;Sun, Xuebing;Feng, Yingcai;Peng, Hao;Wang, Xing;Gao, Yajuan;Liu, Yong;Gong, Wenfeng;Yu, Fenglong;Liu, Xuesong;Wang, Lai;Zhou, Changyou [Journal of Medicinal Chemistry,2020,vol. 63,# 24,p. 15541 - 15563]

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