Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
2.1: sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide / dichloromethane; water / Inert atmosphere; Cooling with ice
3.1: bromine; magnesium / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere
3.2: 20 °C / Inert atmosphere
3.3: 0 °C
4.1: pyridine; N-ethyl-N,N-diisopropylamine / dichloromethane; acetonitrile / 3 h / -15 - 20 °C / Inert atmosphere
5.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N-ethyl-N,N-diisopropylamine; triphenylphosphine / acetonitrile / 20 h / 20 °C / Inert atmosphere
6.1: trimethylaluminum; sodium carbonate / dichloromethane; toluene / 6 h / -20 °C / Inert atmosphere
6.2: 0.25 h / 20 °C / Inert atmosphere
With
pyridine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bromine; trimethylaluminum; sodium hydrogencarbonate; sodium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; triphenylphosphine; potassium bromide;
In
tetrahydrofuran; dichloromethane; water; toluene; acetonitrile;
6.1: Aza-Claisen rearrangement;
DOI:10.1002/ejoc.201200073