Multi-step reaction with 7 steps
1.1: bis(tri-t-butylphosphine)palladium(0) / 1,4-dioxane / 4 h / 100 °C / Inert atmosphere
2.1: tetrahydrofuran / -78 - 25 °C / Inert atmosphere
2.2: Inert atmosphere
3.1: pyridinium hydrobromide perbromide / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
4.1: N,N-dimethyl-formamide / 18 h / 80 °C / Inert atmosphere
5.1: potassium hydroxide / ethanol; water / 2 h / 60 °C / Inert atmosphere
5.2: Inert atmosphere
6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / dichloromethane; N,N-dimethyl-formamide / 1 h / Inert atmosphere
6.2: 23 h / Inert atmosphere
7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere
With
pyridinium hydrobromide perbromide; bis(tri-t-butylphosphine)palladium(0); O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; trifluoroacetic acid; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm201394e