Multi-step reaction with 9 steps
1: sodium cyanide / N,N-dimethyl-formamide / 7 h / 150 °C / Inert atmosphere
2: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 3 h / 110 °C / Inert atmosphere
3: sodium hydroxide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
4: bis-triphenylphosphine-palladium(II) chloride; lithium chloride / 1-methyl-pyrrolidin-2-one / 4 h / 120 °C / Inert atmosphere
5: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
6: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C / Inert atmosphere
7: 10% palladium on activated charcoal; hydrogen / methanol / 2 h / 20 °C
8: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
9: 10% palladium on activated charcoal; hydrogen / 48 h / 20 °C
With
sodium cyanide; bis-triphenylphosphine-palladium(II) chloride; sodium azide; 10% palladium on activated charcoal; hydrogen; ammonium chloride; triethylamine; lithium chloride; sodium hydroxide;
In
1-methyl-pyrrolidin-2-one; methanol; dichloromethane; N,N-dimethyl-formamide;
4: Stille coupling;
DOI:10.1016/j.ejmech.2011.01.014