Multi-step reaction with 11 steps
1.1: sodium hydride / tetrahydrofuran / 2 h / Inert atmosphere; Cooling with ice
1.2: 20 °C / Cooling with ice
2.1: hydrazine hydrate / methanol / 1 h / Reflux
3.1: potassium hydroxide; iodine / N,N-dimethyl-formamide / 4 h / 20 °C
4.1: triethylamine / dmap / tetrahydrofuran / 1.17 h / 20 °C
5.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.25 h / 110 °C / Inert atmosphere
6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 0.5 h / Cooling with ice
6.2: pH 5
7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -10 °C / Inert atmosphere
7.2: 2 h
8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 2 h / 60 °C
8.2: pH 5
9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h / 20 °C
10.1: 1H-imidazole / N,N-dimethyl-formamide / 8 h / 20 °C / Cooling with ice
11.1: sodium hydride / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere; Cooling with ice
With
1H-imidazole; potassium phosphate; water; iodine; sodium hydride; benzotriazol-1-ol; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; potassium hydroxide; sodium hydroxide;
dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;