Multi-step reaction with 11 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: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 20 °C
7.2: 1 h / 20 °C
8.1: tri tert-butylphosphoniumtetrafluoroborate / tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane; dimethyl sulfoxide / 0.75 h / 95 °C / Inert atmosphere
9.1: N-ethyl-N,N-diisopropylamine; methanesulfonyl chloride / dichloromethane / 0.5 h / Cooling with ice
9.2: 5 h / 20 °C
10.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
11.1: water; lithium hydroxide monohydrate / 1,4-dioxane / 0.75 h / 135 °C / Microwave irradiation; Sealed vial
With
hydrogenchloride; dmap; sodium tetrahydroborate; lithium hydroxide monohydrate; ethanol; carbon tetrabromide; water; sodium hydride; caesium carbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium hydroxide; tri tert-butylphosphoniumtetrafluoroborate;
tris-(dibenzylideneacetone)dipalladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; mineral oil;