Multi-step reaction with 10 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 0.92 h / 150 °C / Microwave irradiation
2.1: tetrabutylammomium bromide; palladium diacetate; potassium carbonate / N,N-dimethyl-formamide / 2.25 h / 65 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C
4.2: 0 - 20 °C
5.1: pyridinium p-toluenesulfonate / ethanol / 55 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C
6.2: 0 - 20 °C
7.1: pyridinium p-toluenesulfonate / ethanol / 55 °C
8.1: dmap; triethylamine / dichloromethane / 0 - 20 °C
9.1: tetrabutyl ammonium fluoride / 70 °C
10.1: dimethylsulfide; trifluoroacetic acid / 20 °C
With
dmap; dimethylsulfide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; palladium diacetate; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; caesium carbonate; triethylamine; trifluoroacetic acid;
In
ethanol; dichloromethane; N,N-dimethyl-formamide;
4.1: Williamson synthesis / 4.2: Williamson synthesis;
DOI:10.1021/jm2009106