Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 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; water; diethyl ether / 20 - 60 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.75 h / 0 - 20 °C
4.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 20 - 60 °C / Inert atmosphere
5.1: tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium hydrogencarbonate / butan-1-ol; water / 20 - 100 °C
6.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 24 h
7.1: hydrogenchloride / 1,4-dioxane; ethanol
8.1: caesium carbonate / N,N-dimethyl-formamide / 60 °C
9.1: sodium hydroxide; trimethylsilyl bromide / ethanol; dichloromethane / 3 h / 0 - 80 °C
With
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; 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; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; butan-1-ol;