Multi-step reaction with 9 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C
1.2: 3 h / 0 °C
2.1: potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; 1,4-dioxane / 17 h / 80 °C
3.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 18 h / 85 °C
4.1: palladium on activated charcoal; hydrogen / methanol / 18 h / 20 °C
5.1: trifluoroacetic acid / dichloromethane / 5 h / 0 - 20 °C
6.1: sodium iodide; sodium carbonate / N,N-dimethyl-formamide / 4 h / 90 °C
7.1: hydrazine hydrate / ethanol / 2 h / 70 °C
8.1: dichloromethane / 2 h / Molecular sieve
9.1: sodium tris(acetoxy)borohydride / 2 h / 20 °C
With
1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; palladium on activated charcoal; hydrogen; potassium acetate; sodium tris(acetoxy)borohydride; sodium carbonate; hydrazine hydrate; diisopropylamine; trifluoroacetic acid; sodium iodide;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/j.ejmech.2013.12.056