Multi-step reaction with 11 steps
1: sodium hydroxide / 1,4-dioxane; water / 0.5 h / 0 - 20 °C
2: nitric acid; formic acid / water / 0 - 20 °C
3: sodium hydroxide / 1,4-dioxane / 0 - 20 °C
4: potassium carbonate / N,N-dimethyl-formamide / 70 °C
5: hydrazine hydrate / Raney nickel / water; methanol / 2 h / 20 °C
6: sodium t-butanolate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / toluene / 110 °C
7: pyridinium hydrobromide perbromide / tetrahydrofuran / 60 °C
8: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 100 °C
9: hydrazine hydrate / Raney nickel / methanol / 2 h / 20 °C
10: triethylamine / dichloromethane / 0 - 20 °C
11: boron tribromide / dichloromethane / 0 °C
With
formic acid; pyridinium hydrobromide perbromide; nitric acid; boron tribromide; potassium carbonate; hydrazine hydrate; triethylamine; sodium hydroxide; sodium t-butanolate;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;