Multi-step reaction with 12 steps
1.1: 1 h / 60 °C
1.2: 0.67 h / 180 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C
3.1: sodium hydroxide; bromine; water / 1,4-dioxane / 1.17 h / 0 - 20 °C
3.2: pH 2
4.1: trifluoroacetic acid; methyl-phenyl-thioether / toluene / 18 h
5.1: thionyl chloride / 72 h / 50 °C
6.1: pyridine / 1 h
7.1: N-Bromosuccinimide / dibenzoyl peroxide / tetrachloromethane / 85 °C
8.1: triethylamine / acetone / 1 h
9.1: potassium phosphate / tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 1 h / 120 °C
10.1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 40 °C
11.1: water; lithium hydroxide / tetrahydrofuran / 1 h / 50 °C
12.1: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 3 h
With
pyridine; potassium phosphate; N-Bromosuccinimide; thionyl chloride; 1-hydroxy-7-aza-benzotriazole; methyl-phenyl-thioether; water; bromine; potassium carbonate; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; lithium hydroxide;
tetrakis(triphenylphosphine) palladium(0); dibenzoyl peroxide;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; 1,2-dimethoxyethane; N,N-dimethyl-formamide; acetone; toluene;