Multi-step reaction with 12 steps
1: acetic acid; iron / acetic acid / 0.5 h / 90 °C
2: 0.5 h / 0 - 20 °C
3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,2-dimethoxyethane / 2 h / 90 °C / Inert atmosphere
4: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 12 h / Inert atmosphere
5: potassium fluoride / N,N-dimethyl-formamide / 5 h / 130 °C
6: ammonium chloride; zinc / water; tetrahydrofuran / 0.5 h / 20 °C
7: 0.5 h / 100 °C
8: triethylamine; tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere
9: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C
10: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tetrahydrofuran; dimethyl sulfoxide / 12 h / 20 °C
11: sodium hydroxide / water; ethanol / 2 h / 85 °C
12: pyridine / dichloromethane / 2 h
With
pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); copper(ll) sulfate pentahydrate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; iron; sodium carbonate; ammonium chloride; acetic acid; sodium L-ascorbate; triethylamine; sodium hydroxide; zinc;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;