Multi-step reaction with 10 steps
1.1: acetic acid; Iodine monochloride / 72 h / 20 °C / Inert atmosphere
2.1: triethylamine / water; 1,4-dioxane
2.2: pH 2 - 3
3.1: sodium hydroxide / dichloromethane; water / 3 h / 0 - 20 °C
3.2: pH 2 - 3
4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 20 h / 20 °C / Inert atmosphere
5.1: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h
6.1: trifluoroacetic acid / dichloromethane / 1 h
7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h
8.1: dimethyl amine; 1-thiopropane / tetrahydrofuran / 1 h
9.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h
10.1: potassium carbonate / acetone / 24 h
With
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 1-thiopropane; Iodine monochloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dimethyl amine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; acetone;
4.1: |Sonogashira Cross-Coupling;
DOI:10.1039/c3cc40628h