Multi-step reaction with 12 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 2.83 h / -78 - 20 °C
2.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / 11 h / 90 °C / Inert atmosphere
3.1: pyridine / 6.5 h
4.1: palladium 10% on activated carbon; hydrogen / acetic acid; ethyl acetate / 14 h
5.1: acetic acid / ethanol / 15 h / 20 - 50 °C
6.1: caesium carbonate / acetonitrile / 2 h
7.1: iodine; silver(I) acetate / dichloromethane / 5 h / 20 °C / Darkness
8.1: n-butyllithium; N-fluorobis(benzenesulfon)imide / tetrahydrofuran; hexane / 1 h / -78 °C
9.1: 5%-palladium/activated carbon; hydrogen / ethanol / 8 h / Inert atmosphere
10.1: caesium carbonate / acetonitrile / 3 h
11.1: hydrogenchloride; water / tetrahydrofuran; methanol / 1 h / 50 °C
11.2: 20 °C
12.1: methanol; sodium hydroxide / 1 h / 50 °C
12.2: 20 °C
With
pyridine; hydrogenchloride; methanol; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; 5%-palladium/activated carbon; palladium 10% on activated carbon; water; hydrogen; iodine; silver(I) acetate; caesium carbonate; acetic acid; N-fluorobis(benzenesulfon)imide; sodium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; acetic acid; ethyl acetate; acetonitrile;