Multi-step reaction with 13 steps
1.1: dichloromethane / 0 - 20 °C
2.1: thionyl chloride / 1 h / Reflux
3.1: n-butyllithium / tetrahydrofuran; hexane / 4 h / -78 - -20 °C / Inert atmosphere
3.2: 2.25 h / -78 - 20 °C
4.1: pyridinium p-toluenesulfonate / toluene / Reflux
5.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - -17 °C / Inert atmosphere
5.2: 1.5 h / -78 - 20 °C
6.1: sulfuric acid / methanol; water / Reflux
7.1: hydrazine hydrate / acetic acid / 1.5 h / 50 °C / Inert atmosphere
8.1: potassium acetate; 4,7-dimethoxy-1,10-phenanthroline; copper(l) iodide / 1,4-dioxane / 10 h / 90 °C / Inert atmosphere
9.1: methanol; sodium tetrahydroborate / 1 h / 20 °C
10.1: triethylamine
11.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; XPhos / 1,4-dioxane / 15 h / 65 °C / Inert atmosphere
12.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; acetonitrile / 2 h / 95 °C / Inert atmosphere
13.1: lithium hydroxide monohydrate; water / tetrahydrofuran; isopropyl alcohol / 0.5 h / 35 °C
With
methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; potassium phosphate; copper(l) iodide; n-butyllithium; thionyl chloride; lithium hydroxide monohydrate; 4,7-dimethoxy-1,10-phenanthroline; sulfuric acid; water; potassium acetate; pyridinium p-toluenesulfonate; hydrazine hydrate; triethylamine; XPhos;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetic acid; isopropyl alcohol; toluene; acetonitrile;