Multi-step reaction with 8 steps
1.1: lithium diisopropyl amide / n-heptane; tetrahydrofuran; ethylbenzene / 4.67 h / -70 °C
1.2: 2 h / -70 - 20 °C
2.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1.5 h / Inert atmosphere; Reflux
3.1: thionyl chloride / 18 h / 100 °C / Inert atmosphere
4.1: thiourea; pyridine / isopropyl alcohol / 3 h / Inert atmosphere; Reflux
4.2: 1.5 h / Reflux
5.1: 1-methyl-pyrrolidin-2-one / 0.33 h / 150 °C
6.1: trimethylsilyl bromide / propiononitrile / 20 - 85 °C / Inert atmosphere
7.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 21 h / 80 °C / Inert atmosphere
8.1: hydrogenchloride / 1,4-dioxane / 19 h / 20 - 50 °C / Inert atmosphere
With
pyridine; hydrogenchloride; thionyl chloride; trimethylsilyl bromide; caesium carbonate; thiourea; lithium diisopropyl amide;
tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; n-heptane; ethylbenzene; isopropyl alcohol; propiononitrile;