Multi-step reaction with 10 steps
1.1: N,N-dimethyl-formamide / 2 h / 130 °C / Inert atmosphere
1.2: 1.5 h / 100 °C / Inert atmosphere
2.1: copper(l) iodide / N,N-dimethyl-formamide; methanol / 19 h / 110 °C / Inert atmosphere
3.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: potassium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere
5.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 19 h / 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride; ethylenediamine / tetrahydrofuran / 21 h / 70 °C / Inert atmosphere
7.1: aluminum (III) chloride / nitromethane; dichloromethane / 4 h / 20 °C / Inert atmosphere
8.1: sodium hydroxide; water / methanol / 1 h / 20 °C / Inert atmosphere
9.1: 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere
10.1: 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol; sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; tert-butyl alcohol / 3 h / 20 °C / Inert atmosphere
With
aluminum (III) chloride; copper(l) iodide; copper(ll) sulfate pentahydrate; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; water; sodium hydride; sodium L-ascorbate; ethylenediamine; N-ethyl-N,N-diisopropylamine; 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one; potassium hydroxide; sodium hydroxide; 3-[4-[[bis[[1-(3-hydroxypropyl)triazol-4-yl]methyl]amino]methyl]triazol-1-yl]propan-1-ol;
In
tetrahydrofuran; methanol; nitromethane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;
7.1: |Friedel-Crafts Acylation / 10.1: |Huisgen Cycloaddition;
DOI:10.1021/ml400097z