Multi-step reaction with 9 steps
1.1: sec.-butyllithium / tetrahydrofuran / 0.5 h / -70 - -65 °C / Inert atmosphere
1.2: 1 h / Inert atmosphere
2.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 100 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
4.1: potassium hydroxide; iodine / N,N-dimethyl-formamide / 2 h / 20 °C
5.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C
6.1: caesium carbonate / palladium diacetate; tri-tert-butyl phosphine / toluene; acetonitrile / 0.17 h / 80 °C
7.1: potassium carbonate; methanol / 1 h / 20 °C
8.1: potassium carbonate / 2-methoxy-ethanol / 3 h / 130 °C
9.1: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
With
hydrogenchloride; methanol; dmap; tetrabutyl ammonium fluoride; iodine; sec.-butyllithium; sodium carbonate; potassium carbonate; caesium carbonate; triethylamine; potassium hydroxide;
tetrakis(triphenylphosphine) palladium(0); tri-tert-butyl phosphine; palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene; acetonitrile;