Multi-step reaction with 9 steps
1.1: caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; water / 1 h / 65 °C / Inert atmosphere
2.1: dmap; triethylamine / dichloromethane / 1 h
2.2: 2 h
3.1: ethanol; sodium tetrahydroborate / 0.25 h
4.1: sodium hydroxide; water / methanol / 1.5 h / 45 °C
5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 1 h / 20 °C
5.2: 1 h
6.1: hydrogenchloride / 1,4-dioxane / 1.5 h
6.2: 18 h
7.1: tri tert-butylphosphoniumtetrafluoroborate / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; dimethyl sulfoxide / 0.75 h / 150 °C / Microwave irradiation; Sealed vial; Inert atmosphere
8.1: hydrogen; formic acid / palladium(II) hydroxide / ethanol / Inert atmosphere
9.1: water; lithium hydroxide / 1,4-dioxane / 20 h / 90 °C
With
hydrogenchloride; dmap; sodium tetrahydroborate; formic acid; ethanol; carbon tetrabromide; water; hydrogen; caesium carbonate; triethylamine; triphenylphosphine; sodium hydroxide; lithium hydroxide; tri tert-butylphosphoniumtetrafluoroborate;
tris-(dibenzylideneacetone)dipalladium(0); palladium(II) hydroxide;
In
1,4-dioxane; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide;