Multi-step reaction with 10 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C
1.2: 3.5 h / 20 °C
2.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 60 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
4.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 60 °C / Inert atmosphere
5.1: tris-(dibenzylideneacetone)dipalladium(0); XPhos; sodium hydrogencarbonate / butan-1-ol; water / 100 °C
6.1: palladium 10% on activated carbon; hydrogen / ethanol; tetrahydrofuran / 24 h
7.1: hydrogenchloride / ethanol; 1,4-dioxane / 3 h
8.1: caesium carbonate / N,N-dimethyl-formamide / 1.5 h / 60 °C
9.1: trimethylsilyl bromide / dichloromethane / 0 - 20 °C
9.2: 3 h / 80 °C
10.1: water; methanol / 1 h / 50 °C
With
hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium(0); copper(l) iodide; trimethylsilyl bromide; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; caesium carbonate; triethylamine; XPhos;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; butan-1-ol;