Multi-step reaction with 11 steps
1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C
1.2: 3 h / 20 °C
2.1: tetrabutylammomium bromide; sodium hydroxide / dichloromethane / 1 h / 20 °C
3.1: trifluoroacetic acid / chloroform / 1 h / 0 °C
4.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C
4.2: 96 h / 20 °C
5.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / methanol; water; toluene / 2 h / 90 °C
6.1: tetrabutylammonium hydrogen sulfate / dichloromethane / 2 h / 20 °C
7.1: trifluoroacetic acid / chloroform / 1 h / 0 °C
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one / tetrahydrofuran / 72 h / 0 - 20 °C / Inert atmosphere
9.1: lithium hydroxide monohydrate; dihydrogen peroxide / methanol / 1 h / 0 °C
9.2: 22 h / 20 °C
10.1: trifluoroacetic acid / chloroform / 2 h / 0 °C
11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 3-hydroxy-3,4-dihydrobenzotriazine-4-one / N,N-dimethyl-formamide / 1 h / 0 °C
11.2: 96 h / 20 °C
With
tetrakis(triphenylphosphine) palladium(0); 1-hydroxy-7-aza-benzotriazole; lithium hydroxide monohydrate; tetrabutylammomium bromide; dihydrogen peroxide; sodium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 3-hydroxy-3,4-dihydrobenzotriazine-4-one; triphenylphosphine; tetrabutylammonium hydrogen sulfate; trifluoroacetic acid; sodium hydroxide; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;
5.1: Suzuki coupling;
DOI:10.1002/chem.201103185