Multi-step reaction with 9 steps
1.1: caesium carbonate / triphenylphosphine; palladium diacetate / N,N-dimethyl-formamide / 18 h / 80 °C
2.1: hydrogenchloride; hydrogen / water; methanol / 48 h / 2068.65 Torr / Inert atmosphere
2.2: 20 h / 20 °C
3.1: zinc(II) chloride / diethyl ether; 1,2-dichloro-ethane; tert-butyl alcohol / 0.5 h / 0 °C
3.2: 60 h / 0 - 20 °C
4.1: triethylamine / triphenylphosphine; copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride / N,N-dimethyl-formamide / 0.33 h / 120 °C / microwave irradiation
5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate; ethanol / 42 h / 20 °C / Inert atmosphere
6.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 22 h / 20 - 40 °C
7.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; ammonium carbonate; / N,N-dimethyl-formamide; tetrahydrofuran / 45 h / 20 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere
9.1: sodium tris(acetoxy)borohydride; methanol / water / 1 h / 20 °C / Inert atmosphere
With
hydrogenchloride; methanol; lithium hydroxide monohydrate; water; hydrogen; ammonium carbonate; sodium tris(acetoxy)borohydride; benzotriazol-1-ol; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc(II) chloride;
copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; palladium 10% on activated carbon; palladium diacetate; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;