Multi-step reaction with 10 steps
1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / 0 °C
1.2: 2 h / 20 °C
2.1: Lawessons reagent / toluene / 3 h / 120 °C
3.1: hydrazine hydrate / ethanol / 20 °C
4.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 4 h / 90 °C
5.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / water; N,N-dimethyl-formamide / 80 °C
5.2: chiralpak AD
6.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 760.05 Torr
7.1: tetra-N-butylammonium tribromide / methanol; dichloromethane / 0.5 h / 20 °C
8.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / ethanol / 16 h / 90 °C
9.1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / water; 1,4-dioxane / 90 °C
10.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C
With
Lawessons reagent; hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium(0); dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon; hydrogen; potassium acetate; tetra-N-butylammonium tribromide; potassium hexamethylsilazane; sodium carbonate; hydrazine hydrate;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
5.1: |Suzuki Coupling;
DOI:10.1021/jm5013006