Multi-step reaction with 13 steps
1.1: pyridine / dmap / dichloromethane / 3.33 h / 35 °C / Reflux
2.1: triethylamine / dmap / dichloromethane
3.1: BAST / tetrahydrofuran / 2 h / 20 °C / Cooling with water
4.1: hydrogen bromide; acetic acid / 1 h / 20 °C
5.1: potassium carbonate / dichloromethane; N,N-dimethyl-formamide / 2 h / 20 °C
6.1: sodium methylate / methanol / 12 h / Reflux
7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 20 °C
8.1: N-Bromosuccinimide / acetone / 2 h / 20 °C
9.1: water / ethyl acetate
10.1: acetic anhydride / dimethyl sulfoxide / 20 °C
11.1: n-butyllithium / toluene; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
11.2: 0.5 h / -78 °C
12.1: boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 0.5 h / -40 °C / Inert atmosphere
13.1: hydrogenchloride; hydrogen / palladium 10% on activated carbon / dichloromethane; methanol / 2 h / 4500.45 Torr
With
pyridine; hydrogenchloride; triethylsilane; N-Bromosuccinimide; n-butyllithium; boron trifluoride diethyl etherate; water; hydrogen bromide; hydrogen; sodium methylate; acetic anhydride; sodium hydride; potassium carbonate; acetic acid; triethylamine;
dmap; palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;