Multi-step reaction with 9 steps
1.1: sodium hydrogencarbonate / water; tetrahydrofuran / 0 - 20 °C
2.1: hydrogen / palladium 10% on activated carbon / methanol / 16 h / 20 °C
3.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C
3.2: 0 - 20 °C
4.1: sulfuric acid / 18 h / 105 °C
4.2: 20 °C / pH 13
5.1: triethylamine / 1,1-dichloroethane / Reflux
6.1: diethylamino-sulfur trifluoride / dichloromethane / -78 - 20 °C
7.1: hydrogenchloride; water; acetic acid / 16 h / 110 °C / Sealed tube
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C
9.1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; ethanol; water / 5 h / 90 °C / Inert atmosphere
With
hydrogenchloride; diethylamino-sulfur trifluoride; sulfuric acid; water; hydrogen; sodium hydrogencarbonate; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium nitrite;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; 1,1-dichloroethane; ethanol; dichloromethane; water; toluene;
9.1: Suzuki Coupling;