Multi-step reaction with 9 steps
1.1: iodine; potassium carbonate / water / 20 °C
2.1: potassium carbonate / methanol / 50 °C / Inert atmosphere
3.1: sodium hydride / N,N-dimethyl-formamide / 20 °C
3.2: 1 h / 100 °C / Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C
5.1: potassium carbonate / methanol / 48 h / 20 °C
6.1: bromine / acetic acid / 20 °C
7.1: isopropylmagnesium chloride / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere
7.2: 20 °C
8.1: tetrahydrofuran / 1 h / 0 °C
9.1: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 0.17 h / 155 °C / Microwave irradiation
With
bromine; iodine; isopropylmagnesium chloride; sodium hydride; sodium carbonate; potassium carbonate; trifluoroacetic acid;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2;
In
tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;