Multi-step reaction with 16 steps
1.1: pyridine / 24 h / 20 °C
2.1: nitric acid; sulfuric acid / 0.08 h / -40 °C
3.1: sodium hydroxide / water / 0.08 h
3.2: 85 °C
3.3: pH 2
4.1: water; hydrogen bromide; acetic acid / 4 h / Reflux
5.1: hydrogen / palladium 10% on activated carbon / methanol / 20 °C / 2068.65 Torr
6.1: sodium nitrite; hydrogen bromide / water / 2 h / 0 °C
6.2: 0 - 20 °C
7.1: sulfuric acid / 16 h / Reflux
8.1: caesium carbonate / N,N-dimethyl-formamide / 1 h / 20 °C
8.2: 12 h / 70 °C
9.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 10 h / 80 °C / Inert atmosphere
10.1: water; lithium hydroxide / tetrahydrofuran / 17 h / 20 °C
10.2: pH 2
11.1: thionyl chloride / 2 h / Reflux
12.1: dichloromethane; diethyl ether / 1 h / -10 - 0 °C
12.2: 0.5 h / -10 °C
13.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C
13.2: 12 h / 20 °C
14.1: ammonium acetate / xylene / 16 h / Reflux
15.1: hydrogenchloride / methanol / 4 h / 20 °C
16.1: triethylamine / dichloromethane / 1 h / 20 °C
16.2: 12 h / 20 °C
With
pyridine; hydrogenchloride; thionyl chloride; sulfuric acid; ammonium acetate; water; hydrogen bromide; hydrogen; nitric acid; sodium carbonate; potassium carbonate; caesium carbonate; acetic acid; triethylamine; sodium hydroxide; lithium hydroxide; sodium nitrite;
tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; xylene;
9.1: Suzuki Coupling;