Multi-step reaction with 10 steps
1.1: sulfuric acid / 80 °C / Sealed tube
2.1: potassium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane; water / 4 h / 140 °C / Sealed tube
3.1: hydrogen; acetic acid / platinum(IV) oxide / 60 h / Inert atmosphere
4.1: hydrogenchloride / 1,4-dioxane; water / 3 h / 50 °C
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
6.1: water; potassium carbonate / methanol / 16 h / 20 °C
7.1: 2-chloro-1-methyl-pyridinium iodide / 1-methyl-pyrrolidin-2-one / 1.5 h
7.2: 2 h
8.1: hydrogen / palladium hydroxide, 20 wt% on carbon / ethanol / 16 h / Inert atmosphere
9.1: HATU / N,N-dimethyl acetamide / 0.25 h / 20 °C
9.2: 16 h / 20 °C
10.1: trifluoroacetic acid / dichloromethane / 20 °C
With
hydrogenchloride; sulfuric acid; 2-chloro-1-methyl-pyridinium iodide; water; hydrogen; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid;
platinum(IV) oxide; tetrakis(triphenylphosphine) palladium(0); palladium hydroxide, 20 wt% on carbon;
In
1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; water;
2.1: Suzuki Coupling;