Multi-step reaction with 8 steps
1.1: iron; ammonium chloride / water; ethanol / 2 h / Reflux
2.1: hydrogenchloride; sodium nitrite / water; acetic acid / 1 h / -10 - -5 °C
2.2: 0.5 h / 0 - 10 °C
3.1: ammonia / dichloromethane; methanol / 0.08 h / 0 - 20 °C
4.1: dmap / dichloromethane / 20 °C / Reflux
5.1: lithium hydroxide; water / tetrahydrofuran / 20 °C
6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C
7.1: trifluoroacetic acid / trifluoroacetic acid / 2 h / 20 °C
8.1: tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 85 °C
With
hydrogenchloride; dmap; tris-(dibenzylideneacetone)dipalladium(0); ammonia; water; iron; ammonium chloride; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; trifluoroacetic acid; lithium hydroxide; sodium nitrite;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; trifluoroacetic acid;