Multi-step reaction with 11 steps
1.1: acetic acid; iron / 4 h
2.1: pyridine / 18 h / 20 °C
2.2: Cooling with ice
3.1: lithium hydroxide / water; tetrahydrofuran; methanol / 15 h / 20 °C
4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 96 h / 110 °C
4.2: 15 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 120 h / 20 °C
7.1: potassium acetate / tricyclohexylphosphine; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 0.33 h / 135 °C / Microwave irradiation
8.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane; water / 0.33 h / 100 °C / Microwave irradiation
9.1: acetic acid; iron / 14 h
10.1: water; sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 0.33 h / 120 °C / Microwave irradiation
11.1: trifluoroacetic acid / dichloromethane
With
pyridine; water; potassium acetate; iron; sodium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium hydroxide;
tris-(dibenzylideneacetone)dipalladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; tricyclohexylphosphine;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;