Multi-step reaction with 8 steps
1.1: pyridine; trifluoroacetic anhydride / 1,2-dimethoxyethane / 3.5 h / 0 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere
2.1: trifluoroacetic acid; methoxybenzene / dichloromethane / Inert atmosphere
3.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 1 h / 20 °C / Inert atmosphere
4.1: trifluoroacetic acid; methoxybenzene / dichloromethane / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 1 h / 20 °C / Inert atmosphere
6.1: lithium hydroxide; dihydrogen peroxide / ethanol / 0 °C / Inert atmosphere
6.2: pH 1 / Inert atmosphere
7.1: trifluoroacetic acid; methoxybenzene / dichloromethane / Inert atmosphere
8.1: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride / dichloromethane / Inert atmosphere
With
pyridine; dihydrogen peroxide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; methoxybenzene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; trifluoroacetic anhydride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride; lithium hydroxide;
In
1,2-dimethoxyethane; ethanol; dichloromethane;
DOI:10.1016/j.tetlet.2014.02.106