Multi-step reaction with 9 steps
1: triethylamine / dichloromethane / 1 h / 20 °C
2: lithium borohydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
3: triethylamine / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere
4: sodium iodide / 20 h / 50 °C
5: N-ethyl-N,N-diisopropylamine / acetonitrile / 3 h / 20 °C
6: sodium tungstate (VI) dihydrate; sulfuric acid / 1,4-dioxane; water; methanol / 4 h / 55 °C
7: tetrabutylammomium bromide; sodium hydroxide / water / 4 h / 60 - 70 °C
8: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; N,N-dimethyl-formamide; ethanol; 1,2-dimethoxyethane / 5 h / 80 - 95 °C / Inert atmosphere
9: sodium carbonate / 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
With
bis-triphenylphosphine-palladium(II) chloride; lithium borohydride; sodium tungstate (VI) dihydrate; sulfuric acid; tetrabutylammomium bromide; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm501778s