Multi-step reaction with 7 steps
1: sodium hydride / N,N-dimethyl-formamide
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 50 °C / Inert atmosphere
3: oxalic acid / methanol; water / 72 h / 55 °C
4: tributylphosphine; 1,1'-azodicarbonyl-dipiperidine / benzene / 18 h / 0 - 50 °C
5: tetrakis(triphenylphosphine)platinum / N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere
6: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 18 h / 80 °C / Inert atmosphere
7: 3,5-dimethoxyphenol; potassium hydroxide; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 18 h / 80 °C / Inert atmosphere
With
bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); 3,5-dimethoxyphenol; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; tetrakis(triphenylphosphine)platinum; tributylphosphine; oxalic acid; sodium hydride; triethylamine; potassium hydroxide; 1,1'-azodicarbonyl-dipiperidine;
In
tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; benzene;
2: |Sonogashira Cross-Coupling / 4: |Mitsunobu Displacement;
DOI:10.1021/jm401616g