Multi-step reaction with 12 steps
1.1: potassium carbonate / acetone / 9 h / Inert atmosphere; Reflux
2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 2 h / -78 - 20 °C
2.3: pH 3
3.1: dichloromethane / 26 h / 20 °C
4.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere
5.1: potassium hydroxide / ethanol; water / 2 h / Reflux
6.1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Reflux
7.1: quinoline; copper(II) oxide / 0.17 h / 220 °C / Inert atmosphere
8.1: boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 1.5 h / -40 °C / Inert atmosphere
9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 30 h / Reflux
10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 7 h / 20 °C
11.1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
12.1: hydrogenchloride / methanol / 12 h / 30 °C
With
quinoline; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon; boron trifluoride diethyl etherate; hydrogen; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium carbonate; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; copper(II) oxide; potassium hydroxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;
4.1: Suzuki-Miyaura coupling;
DOI:10.1016/j.bmc.2011.10.030