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ChemicalBook CAS DataBase List GNE-495

GNE-495 synthesis

8synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 9 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; 1,4-dioxane / 3 h / 80 - 100 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / Reflux
3.1: triethylamine / acetonitrile / 12 h / Inert atmosphere; Reflux
4.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
4.2: 4 h / Inert atmosphere; Reflux
5.1: lithium chloride / dimethyl sulfoxide; water / 100 °C
6.1: N,N-dimethyl-formamide / 80 °C
7.1: ammonium acetate; acetic acid / 80 - 100 °C
8.1: sodium hydroxide / water; tetrahydrofuran; methanol / 2 h / 65 °C
8.2: pH 8
9.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

References:

Vitorino, Philip;Yeung, Stacey;Crow, Ailey;Bakke, Jesse;Smyczek, Tanya;West, Kristina;McNamara, Erin;Eastham-Anderson, Jeffrey;Gould, Stephen;Harris, Seth F.;Ndubaku, Chudi;Ye, Weilan [Nature,2015,vol. 519,# 7544,p. 425 - 430]