Multi-step reaction with 11 steps
1.1: bromine / acetic acid / 20 °C
2.1: potassium carbonate / acetone / 6 h / 20 °C
3.1: nitric acid; sulfuric acid / 0 °C
4.1: hydrogenchloride; tin(II) chloride hydrate / ethanol / 20 °C
4.2: pH 6 - 7
5.1: 20 °C
6.1: sodium hydride / tetrahydrofuran; mineral oil / 20 °C
6.2: 20 °C
7.1: N-ethyl-N,N-diisopropylamine; tetrabutylammomium bromide / palladium diacetate / N,N-dimethyl-formamide / 3 h / 80 °C / Inert atmosphere
8.1: potassium hydroxide; water / 1 h / 20 °C / Reflux
8.2: pH 5
9.1: HATU / tetrahydrofuran / 0 °C
9.2: 20 °C
10.1: potassium hydroxide / N,N-dimethyl-formamide / 20 °C
11.1: caesium carbonate / tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / Inert atmosphere; Reflux
With
hydrogenchloride; tin(II) chloride hydrate; sulfuric acid; tetrabutylammomium bromide; water; bromine; nitric acid; sodium hydride; potassium carbonate; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; potassium hydroxide;
tetrakis(triphenylphosphine) palladium(0); palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; acetic acid; N,N-dimethyl-formamide; acetone; mineral oil;