Multi-step reaction with 10 steps
1.1: toluene-4-sulfonic acid; hydrazine hydrate / 21 h / 120 °C / Cooling with ice
2.1: potassium hydroxide; iodine / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice
3.1: sodium hydride / N,N-dimethyl-formamide / 3 h / Cooling with ice
3.2: 1 h / 20 °C / Cooling with ice
4.1: triethylamine / triphenylphosphine; palladium diacetate / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere
5.1: sodium hydroxide; water / ethanol; tetrahydrofuran / 2 h / 20 °C / Cooling with ice
5.2: Cooling with ice
6.1: trifluoroacetic acid / 16 h / Reflux
7.1: hydrogen / palladium 10% on activated carbon / water; tetrahydrofuran; methanol / 3 h / 20 °C
8.1: N-chloro-succinimide; triphenylphosphine / tetrahydrofuran / 0.03 h / 20 °C
8.2: 7 h / Reflux
9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 20 °C
10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; HATU / N,N-dimethyl-formamide; tetrahydrofuran / 17 h / 20 °C
With
N-chloro-succinimide; water; hydrogen; iodine; sodium hydride; toluene-4-sulfonic acid; hydrazine hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; HATU; trifluoroacetic acid; potassium hydroxide; sodium hydroxide;
palladium 10% on activated carbon; palladium diacetate; triphenylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide;