Multi-step reaction with 9 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 25 °C
1.2: 2 h / 20 °C
2.1: tert.-butyl lithium / tetrahydrofuran / -78 °C
2.2: -78 °C
3.1: triethylamine; copper(l) iodide / trans-bis(triphenylphosphine)palladium dichloride / 1,4-dioxane / 1.5 h / 80 °C
4.1: trifluoroacetic acid / 1,2-dichloro-ethane / 5 h / 20 °C
5.1: potassium carbonate; sodium acetate; copper(II) choride dihydrate / palladium dichloride / 20 °C / 15514.9 Torr / Parr bomb
6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 2 h / 60 °C
7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide; tetrahydrofuran / 20 °C
8.1: hydrogen / palladium 10% on activated carbon / tetrahydrofuran / 0.33 h / 20 °C
9.1: pyridine / 0 - 20 °C
With
pyridine; copper(l) iodide; copper(II) choride dihydrate; water; hydrogen; tert.-butyl lithium; sodium acetate; sodium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; sodium hydroxide;
trans-bis(triphenylphosphine)palladium dichloride; palladium 10% on activated carbon; palladium dichloride;
In
tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;