Multi-step reaction with 12 steps
1.1: nitric acid; sulfuric acid / 0.42 h / cooling with ice
2.1: nitric acid; sulfuric acid / 6 h / 50 °C / cooling with ice
3.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; water / 6 h / Inert atmosphere; Reflux
4.1: acetic acid / 60 °C
4.2: 0.08 h / 60 °C
5.1: phosphorus trichloride / chloroform / 1 h / 60 °C
6.1: sodium hydroxide; water / ethanol / 15 h / 90 °C
7.1: pyridine; trichlorophosphate / tetrahydrofuran / 1 h / 0 °C
8.1: water; ammonium chloride; iron / ethanol / 1.5 h / 80 °C
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C
10.1: potassium carbonate / acetonitrile / 16 h / 80 °C
11.1: potassium hydroxide / tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / 1,4-dioxane; water / 4 h / 100 °C / Inert atmosphere
12.1: potassium carbonate / N,N-dimethyl-formamide / 0.75 h / 60 °C
With
pyridine; sulfuric acid; water; nitric acid; iron; sodium carbonate; potassium carbonate; ammonium chloride; acetic acid; N-ethyl-N,N-diisopropylamine; potassium hydroxide; sodium hydroxide; trichlorophosphate; phosphorus trichloride;
tris-(dibenzylideneacetone)dipalladium(0); tetrakis(triphenylphosphine) palladium(0); tert-butyl XPhos;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;
3.1: Suzuki Coupling;