Multi-step reaction with 12 steps
1: potassium carbonate / N,N-dimethyl-formamide / 50 °C
2: N,N-dimethyl-aniline / 18 h / 210 °C
3: hydrogen; palladium 10% on activated carbon / methanol / 24 h / 20 °C
4: potassium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 80 °C
5: sodium hydroxide / water; ethanol / 2 h / 0 °C / Reflux
6: thionyl chloride / 2 h / Reflux
7: tetramethylammonium fluoride / 1,2-dimethoxyethane / -78 - 20 °C / Inert atmosphere
8: sodium hydride / tetrahydrofuran / 0 - 20 °C
9: hydrogen; palladium 10% on activated carbon / methanol / 20 °C
10: potassium carbonate / N,N-dimethyl-formamide / 20 °C
11: N,N-dimethyl-formamide / 20 °C
12: hydrogenchloride / ethyl acetate / 20 °C
With
hydrogenchloride; thionyl chloride; palladium 10% on activated carbon; tetramethylammonium fluoride; hydrogen; sodium hydride; potassium carbonate; sodium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; water; ethyl acetate; N,N-dimethyl-aniline; N,N-dimethyl-formamide;
2: |Claisen Rearrangement;
DOI:10.1016/j.bmcl.2015.04.080