Multi-step reaction with 9 steps
1: iron; acetic acid / 2 h / 85 °C
2: sulfuric acid; water; sodium nitrite / 19 h / 0 - 60 °C
3: potassium carbonate / acetone / 4 h / Reflux
4: bis-triphenylphosphine-palladium(II) chloride; N,N-dimethyl acetamide; potassium acetate / 40 h / 100 °C / Inert atmosphere
5: aluminum (III) chloride / dichloromethane / 2 h / 0 °C
6: triethylamine / dichloromethane / 0.75 h / 0 °C
7: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; water / 16 h / 90 °C / Inert atmosphere
8: water; sodium hydroxide / ethanol / 3 h / 60 °C
9: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C
With
aluminum (III) chloride; bis-triphenylphosphine-palladium(II) chloride; tetrakis(triphenylphosphine) palladium(0); N,N-dimethyl acetamide; sulfuric acid; water; potassium acetate; iron; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; sodium nitrite;
In
1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
4: |Sonogashira Cross-Coupling / 7: |Suzuki Coupling;