Multi-step reaction with 8 steps
1: trichlorophosphate / 3 h / 100 °C / Inert atmosphere
2: ammonium hydroxide; 1-methyl-pyrrolidin-2-one / water / 20 h / 148 °C / Sealed tube
3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux
4: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere
5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr
6: dmap; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere
7: sodium hydroxide / water; methanol; tetrahydrofuran / 20 °C
8: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 20 °C / Inert atmosphere
With
1-methyl-pyrrolidin-2-one; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; ammonium hydroxide; N-Bromosuccinimide; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; trichlorophosphate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/acsmedchemlett.5b00174