Multi-step reaction with 13 steps
1.1: potassium hydroxide / water; tetrahydrofuran / 0 - 20 °C
2.1: diphenylether / 240 - 250 °C / Inert atmosphere
3.1: sodium hydroxide; water / methanol / 2 h / Inert atmosphere; Reflux
4.1: sodium hydroxide / water / 4 h / 100 °C
4.2: 20 °C / pH 4 - 5
5.1: sodium hydroxide / diphenylether; water / 6 h / 100 °C
5.2: 20 °C / pH 4 - 5
6.1: copper; quinoline / 1.5 h / 210 - 220 °C / Inert atmosphere
7.1: bromine / tetrachloromethane / 2.5 h / 0 °C
8.1: sodium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / tetrahydrofuran / 80 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C
9.2: 1 h
10.1: boron tribromide / dichloromethane / 0.5 h / 0 °C
10.2: Cooling with ice
11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C
12.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 80 °C / Inert atmosphere
13.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere
With
quinoline; n-butyllithium; water; bromine; potassium acetate; boron tribromide; copper; sodium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; potassium hydroxide; sodium hydroxide;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; hexanes; diphenylether; dichloromethane; water;
8.1: Suzuki Coupling / 13.1: Suzuki Coupling;