Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C
1.2: 0 - 20 °C
1.3: 16 h / 20 °C
2.1: thionyl chloride / 1,2-dichloro-ethane / 116 h / Reflux; Inert atmosphere
3.1: thiourea; pyridine / isopropyl alcohol / 17 h / Reflux
3.2: 1 h / Reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 5 h / 20 °C / Inert atmosphere
5.1: phosphorus(V) oxybromide / 1,2-dichloro-ethane / 3 h / 70 °C
6.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 4.5 h / 75 °C / Inert atmosphere
7.1: N,N,N,N,-tetramethylethylenediamine / 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide / 0.33 h / 140 °C / Inert atmosphere; Microwave irradiation
8.1: water; formic acid; nickel/aluminium alloy / 4 h / 100 °C
9.1: sodium tetrahydroborate / methanol / 0 - 20 °C
9.2: 1 h / 20 °C
With
pyridine; sodium tetrahydroborate; formic acid; thionyl chloride; N,N,N,N,-tetramethylethylenediamine; nickel/aluminium alloy; water; sodium hydride; caesium carbonate; thiourea; 3-chloro-benzenecarboperoxoic acid; phosphorus(V) oxybromide;
1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol;