Multi-step reaction with 12 steps
1: N-ethyl-N,N-diisopropylamine / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethyl acetate / 27 h / 90 °C
2: sodium hydroxide; water / methanol / 1 h / 25 °C
3: sulfuric acid; potassium nitrate / 1.17 h / 0 - 50 °C
4: methanol / 22 h / 20 - 50 °C
5: ammonium formate / 5%-palladium/activated carbon / ethanol / 62 h / 75 °C
6: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / Heating / reflux
7: dichloromethane; N,N-dimethyl-formamide / 16.25 h / 0 - 20 °C / Heating / reflux
8: N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 8 h / 100 °C
9: ammonium formate / palladium 10% on activated carbon / ethanol / 1 h / 75 °C
10: isopropylmagnesium chloride / tetrahydrofuran / 1.33 h / 20 °C
11: caesium carbonate / acetonitrile / 16 h / 80 °C
12: 1,4-dioxane / 16 h / 100 °C
With
sodium hydroxide; sulfuric acid; water; isopropylmagnesium chloride; ammonium formate; caesium carbonate; potassium nitrate; N-ethyl-N,N-diisopropylamine;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 5%-palladium/activated carbon; palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;