Multi-step reaction with 8 steps
1: thionyl chloride / 3 h / Reflux
2: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 26 h / 20 °C
3: thionyl chloride / dichloromethane / 2.5 h / 20 °C
4: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 85 °C
5: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C
6: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 4 h / 150 °C / Microwave irradiation
7: trifluoroacetic acid / 4 h / Reflux
8: potassium carbonate / N,N-dimethyl-formamide / 6 h / 20 °C
With
thionyl chloride; palladium 10% on activated carbon; hydrogen; palladium diacetate; potassium carbonate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2014.05.066