Multi-step reaction with 11 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 2.83 h / -78 - 20 °C
2.1: acetic acid / ethanol / 7 h / 50 °C
3.1: caesium carbonate / tetrahydrofuran; acetonitrile / 4 h
4.1: pyridine / 18 h
5.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 0.17 h / 0 °C / Cooling with ice
6.1: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane; water / 24 h / 90 °C / Inert atmosphere
7.1: palladium 10% on activated carbon; hydrogen / ethanol / 9 h / Inert atmosphere
8.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / dichloromethane / 3 h / -50 °C
9.1: caesium carbonate / acetonitrile / 4 h
10.1: hydrogenchloride; water / tetrahydrofuran; methanol / 1.5 h / 60 °C
10.2: 20 °C
11.1: methanol; sodium hydroxide / 2 h / 60 °C
11.2: 20 °C
With
pyridine; hydrogenchloride; methanol; triethylsilane; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; caesium carbonate; acetic acid; sodium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; acetonitrile;