Multi-step reaction with 10 steps
1.1: thionyl chloride / 3 h / 0 °C / Reflux
2.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 30 °C
3.1: ammonium chloride; iron / water; methanol / 5 h / Reflux
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane / 20 °C
5.1: phosphorus(V) oxybromide / acetonitrile / Reflux
5.2: pH 7 - 8
6.1: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 100 °C
7.1: sodium hydride / tetrahydrofuran / 1 h / 20 °C
7.2: 3 h / 20 °C
8.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere
8.2: 3 h / 0 - 20 °C
9.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C
9.2: pH 9
10.1: triethylamine / dichloromethane / 3 h / 20 °C
With
thionyl chloride; iron; sodium hydride; potassium carbonate; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorus(V) oxybromide;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;