Multi-step reaction with 8 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
2.1: copper(l) iodide / 1-methyl-pyrrolidin-2-one / 5 h / 150 °C
3.1: hydrogen; 10% Pd/C / ethanol / Inert atmosphere
4.1: N-ethyl-N,N-diisopropylamine; N,N-phenylbistrifluoromethane-sulfonimide / N,N-dimethyl-formamide / 20 °C
4.2: 0.5 h / 110 °C / Microwave irradiation
5.1: hydrogen; 10% Pd/C / ethanol / Inert atmosphere
6.1: lithium hydroxide monohydrate / methanol; water / 40 °C
6.2: pH 5
7.1: 2-chloro-1-methyl-pyridinium iodide / 1-methyl-pyrrolidin-2-one / 0.5 h / 20 °C
7.2: 20 °C
8.1: hydrogenchloride / methanol; 1,4-dioxane / 6 h / 20 °C
With
hydrogenchloride; copper(l) iodide; N,N-phenylbistrifluoromethane-sulfonimide; lithium hydroxide monohydrate; 10% Pd/C; 2-chloro-1-methyl-pyridinium iodide; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine;
In
1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; ethanol; water; N,N-dimethyl-formamide;
4.2: |Suzuki Coupling;
DOI:10.1021/jm300601d