Multi-step reaction with 11 steps
1.1: tetrahydrofuran / 0.5 h / 0 °C
2.1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4 h / 90 °C / Inert atmosphere
3.1: trifluoroacetic acid / tetrahydrofuran / 3 h / Reflux
4.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
5.1: acetic acid; zinc / tetrahydrofuran / 0.25 h / 0 °C
6.1: sodium nitrite; hydrogenchloride / water / 0.25 h / 0 °C
6.2: 0.25 h / 0 °C
7.1: 3 h / Reflux
8.1: sodium hydroxide; water / methanol; tetrahydrofuran / 0.5 h / 20 °C
9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 6 h / 20 °C
10.1: tetrahydrofuran / 0.25 h / -78 °C
11.1: acetonitrile / 6 h / Reflux
With
hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); water; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; sodium hydroxide; sodium t-butanolate; zinc; sodium nitrite;
In
tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile;