Multi-step reaction with 9 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / Inert atmosphere
1.2: 2 h / -78 - 20 °C
2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 16 h / 0 - 20 °C / Inert atmosphere
3.1: tetrahydrofuran / 1 h / -78 - 20 °C
4.1: trifluoroacetic acid / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 2.25 h / -20 - 20 °C / Inert atmosphere
6.1: sodium hydroxide / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere; Sealed tube
7.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran; water / 12 h / Inert atmosphere; Reflux
8.1: phosphorus(V) oxybromide / 2 h / 110 °C / Inert atmosphere
9.1: tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate / toluene / 20 h / Inert atmosphere; Reflux
With
tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); n-butyllithium; potassium carbonate; benzotriazol-1-ol; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; sodium t-butanolate; phosphorus(V) oxybromide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;