Multi-step reaction with 11 steps
1.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / 0 - 20 °C
2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C / Inert atmosphere
3.1: bromine / dichloromethane; acetic acid / 20 °C / Inert atmosphere
4.1: potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
4.2: 3.17 h / 20 - 90 °C / Inert atmosphere
5.1: hydrogenchloride / methanol; isopropyl alcohol / 20 °C
6.1: acetic anhydride / 0.5 h / 20 °C
6.2: 16 h / 60 °C
7.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 16 h / 20 °C
8.1: ammonium acetate / acetic acid / 1 h / Reflux
9.1: trifluorormethanesulfonic acid / toluene / 2 h / Reflux
10.1: sodium hydride; lithium bromide / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere
10.2: 20 - 50 °C / Inert atmosphere
11.1: boron tribromide / dichloromethane / 0 °C / Inert atmosphere
With
hydrogenchloride; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); trifluorormethanesulfonic acid; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; ammonium acetate; hydrogen; bromine; acetic anhydride; boron tribromide; sodium hydride; potassium carbonate; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium iodide; lithium bromide;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; isopropyl alcohol; toluene;