Multi-step reaction with 11 steps
1.1: diphenyl phosphoryl azide / toluene / 3 h / 110 °C / Inert atmosphere
2.1: trifluoroacetic acid / dichloromethane / 5 h / 20 °C
2.2: NH2 cartridge
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h
3.2: 18 h
4.1: thionyl chloride / 18 h / Reflux
5.1: thiourea; pyridine / isopropyl alcohol / 16 h / Inert atmosphere; Reflux
5.2: 6.5 h / Reflux
6.1: trimethylsilyl bromide / propiononitrile / 48 h / 90 °C
7.1: potassium phosphate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / toluene; water / 3 h / 80 °C / Inert atmosphere
8.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
9.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / 1,4-dioxane / 1 h / 80 °C / Inert atmosphere
10.1: ammonia; sodium tetrahydroborate; cobalt(II) chloride hexahydrate / 0.25 h / 0 °C
11.1: hydrogenchloride / 1,4-dioxane / 3 h / 45 °C / Inert atmosphere
With
pyridine; hydrogenchloride; sodium tetrahydroborate; potassium phosphate; thionyl chloride; cobalt(II) chloride hexahydrate; trimethylsilyl bromide; diphenyl phosphoryl azide; ammonia; sodium hydride; caesium carbonate; thiourea; trifluoroacetic acid;
tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; isopropyl alcohol; toluene; propiononitrile; mineral oil;