Multi-step reaction with 9 steps
1.1: potassium carbonate / ethanol / 2.5 h / 20 °C
1.2: 0 °C
2.1: sulfuric acid / dichloromethane / 2.5 h / 0 - 20 °C
3.1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
4.1: hydrogen bromide; acetic acid / water / 110 °C / Inert atmosphere
5.1: pyridine / dichloromethane / 1 h / 0 °C
6.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 80 °C / Inert atmosphere
7.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; N,N-dimethyl-formamide / 2.5 h / 90 °C / Inert atmosphere
8.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / 1,2-dichloro-ethane / Reflux
9.1: methanol / 1 h / Reflux
With
pyridine; methanol; sulfuric acid; hydrogen bromide; potassium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; caesium carbonate; acetic acid;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
ethanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; diethylamine; N,N-dimethyl-formamide; isopropyl alcohol;