Multi-step reaction with 10 steps
1.1: copper(l) iodide; triethylamine / bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Sealed flask
2.1: iodine / dichloromethane / 5 h / Reflux
3.1: triethylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / methanol; acetonitrile / 16 h / 80 °C
4.1: iron; ammonium chloride / tetrahydrofuran; ethanol; water / 3 h / 95 °C
5.1: pyridine / dichloromethane / 16 h / 10 - 15 °C
6.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 50 °C / Inert atmosphere
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
7.2: 0.33 h / 20 °C / Inert atmosphere
8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C
9.1: dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9.2: 0 - 20 °C / Inert atmosphere
10.1: [bis(acetoxy)iodo]benzene; potassium carbonate / dimethyl sulfoxide / 3 h / 20 °C / Inert atmosphere
With
pyridine; copper(l) iodide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; [bis(acetoxy)iodo]benzene; iodine; iron; potassium carbonate; ammonium chloride; 4-methylmorpholine N-oxide; triethylamine;
bis-triphenylphosphine-palladium(II) chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;