Multi-step reaction with 12 steps
1.1: triethylamine; diphenylphosphoranyl azide / toluene / 1.5 h / 90 °C
1.2: 3.5 h / 90 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 20 °C
3.1: N,N-dimethyl-formamide; water / 24 h / 20 °C
4.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C
5.1: sodium hydrogencarbonate / water; 1,4-dioxane / 1.5 h / 0 °C
6.1: acetic acid / toluene / 4 h / 130 °C / Dean-Stark
6.2: 16 h / 20 °C / Dean-Stark
7.1: triethylamine / dichloromethane / 6.25 h / 20 - 40 °C / Cooling with ice
8.1: caesium carbonate; thiophenol / acetonitrile / 2.5 h / 20 °C
9.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 20 °C
10.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 2 h / Cooling with ice
11.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 18 h / 20 °C / Cooling with ice
12.1: trifluoroacetic acid / dichloromethane / 0.25 h / 20 °C
With
hydrogenchloride; lithium hydroxide monohydrate; palladium 10% on activated carbon; diphenylphosphoranyl azide; hydrogen; sodium hydrogencarbonate; caesium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; acetic acid; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/j.bmc.2013.06.057