Multi-step reaction with 11 steps
1.1: iron; ammonium chloride / methanol; tetrahydrofuran; water / 3 h / Reflux
2.1: lithium hydroxide monohydrate; water / 1,4-dioxane / 2 h / Reflux
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 25 °C
3.2: 2 h
4.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
4.2: 1 h / -78 °C
5.1: N-iodo-succinimide / acetonitrile / 0 - 25 °C
6.1: pyridine / 1.5 h / 0 - 25 °C
7.1: potassium carbonate / N,N-dimethyl-formamide / 1 h / 0 - 80 °C / Inert atmosphere
8.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere
9.1: diethylamino-sulfur trifluoride / dichloromethane / 5 h / -78 - 25 °C
10.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / water; 1,4-dioxane / 3 h / 130 °C / Inert atmosphere
11.1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / water; 1,4-dioxane / 2 h / 100 °C / Inert atmosphere
With
pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium(0); N-iodo-succinimide; lithium hydroxide monohydrate; diethylamino-sulfur trifluoride; water; potassium acetate; iron; sodium carbonate; potassium carbonate; ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; XPhos;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
8.1: |Suzuki Coupling / 11.1: |Suzuki Coupling;