Multi-step reaction with 15 steps
1.1: bromine / acetic acid / 20 °C
2.1: trichlorophosphate; N,N-dimethyl-formamide / 2 h / 120 °C
3.1: potassium carbonate / 2 h / Reflux
4.1: triethylamine; triethylsilane; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / N,N-dimethyl-formamide / 12 h / 90 °C / 7500.75 Torr / Autoclave
5.1: n-butyllithium / tetrahydrofuran / -78 °C
5.2: -78 °C
6.1: manganese(IV) oxide / dichloromethane / 50 °C
7.1: hydrogenchloride / water; methanol / 0 - 20 °C
8.1: thionyl chloride / Reflux
9.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / acetonitrile; water / 60 °C / Inert atmosphere
10.1: hydrogen; palladium 10% on activated carbon / tetrahydrofuran; methanol / 20 °C / 760.05 Torr
11.1: manganese(IV) oxide / dichloromethane / 50 °C
12.1: hydrogenchloride / acetic acid; water / 4 h / 110 °C
13.1: triethylamine / methanol / 1 h / 20 °C
14.1: dmap / tetrahydrofuran / 3 h / 70 °C
15.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
With
hydrogenchloride; triethylsilane; dmap; manganese(IV) oxide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; thionyl chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; palladium 10% on activated carbon; hydrogen; bromine; sodium carbonate; potassium carbonate; triethylamine; N,N-dimethyl-formamide; trifluoroacetic acid; trichlorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;