Multi-step reaction with 9 steps
1.1: iron; acetic acid / 2 h / 85 °C
2.1: sulfuric acid; water; sodium nitrite / 19 h / 0 - 60 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
3.2: 1 h / 20 °C
4.1: tetrafluoroboric acid; N,N-dimethyl acetamide; palladium diacetate; potassium carbonate; tricyclohexylphosphine / 100 °C / Inert atmosphere
5.1: aluminum (III) chloride / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C
7.1: 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine / N,N-dimethyl-formamide / 2 h / 80 °C
8.1: water; sodium hydroxide / methanol / 2 h / 60 °C
9.1: triethylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
With
aluminum (III) chloride; tetrafluoroboric acid; N,N-dimethyl acetamide; sulfuric acid; 1,3-bis-(diphenylphosphino)propane; water; palladium diacetate; iron; sodium hydride; potassium carbonate; acetic acid; triethylamine; HATU; sodium hydroxide; sodium nitrite; tricyclohexylphosphine;
In
methanol; dichloromethane; N,N-dimethyl-formamide;
4.1: |Sonogashira Cross-Coupling;