Multi-step reaction with 10 steps
1: lithium hydroxide monohydrate; water / tetrahydrofuran / 48 h / 50 °C
2: polyphosphoric acid; celite / toluene / 5 h / 110 °C
3: N,N-dimethyl-formamide / 20 °C
4: potassium carbonate / N,N-dimethyl-formamide / 50 °C
5: lithium hydroxide monohydrate; water / tetrahydrofuran / 3 h / 50 °C
6: thionyl chloride / 2 h / 80 °C
7: pyridine / tetrahydrofuran / 0 - 20 °C
8: caesium carbonate / N,N-dimethyl-formamide / 20 °C
9: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 48 h / 70 °C / 2585.81 Torr
10: lithium hydroxide monohydrate; water / tetrahydrofuran / 2 h / 20 °C
With
pyridine; 1,1'-bis-(diphenylphosphino)ferrocene; thionyl chloride; lithium hydroxide monohydrate; water; palladium diacetate; potassium carbonate; caesium carbonate; triethylamine;
In
tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm2007084