Multi-step reaction with 11 steps
1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
2.1: sodium hydride; ethanol / 0 - 20 °C
3.1: water / acetonitrile / 3.5 h / Reflux
4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C
5.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / tetrahydrofuran; water / 1 h / Reflux
6.1: bromine / tetrachloromethane / 0.17 h / 0 °C
6.2: 0.33 h / 0 °C
7.1: triethylamine / dichloromethane / 0 - 20 °C
8.1: bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / water; 1,4-dioxane / 1 h / Reflux
9.1: trifluoroacetic acid / dichloromethane / 0.08 h / 0 °C
10.1: dmap / dichloromethane / 2 h / 20 °C
11.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 6 h / 0 - 20 °C
With
dmap; bis-triphenylphosphine-palladium(II) chloride; ethanol; carbon tetrabromide; water; bromine; sodium hydride; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tet.2013.04.039