Multi-step reaction with 12 steps
1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 3 h / -78 °C
2: pyridinium p-toluenesulfonate; copper(II) sulfate / dichloromethane / 24 h
3: tetrahydrofuran / -78 - 20 °C
4: hydrogenchloride / 1,4-dioxane / 2 h / 0 °C
5: triethylamine / dichloromethane / 20 °C
6: dipyridinium dichromate / N,N-dimethyl-formamide / 24 h / 20 °C
7: lithium hydroxide monohydrate; dihydrogen peroxide / water; tetrahydrofuran / 20 °C
8: sodium hydrogencarbonate / dimethyl sulfoxide / 24 h
9: dichloromethane / 2 h / 0 °C
10: 1-hydroxy-7-aza-benzotriazole; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 15 h / 0 - 20 °C
11: hydrogenchloride / 1,4-dioxane / 2 h
12: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane
With
hydrogenchloride; dipyridinium dichromate; 1-hydroxy-7-aza-benzotriazole; oxalyl dichloride; lithium hydroxide monohydrate; dihydrogen peroxide; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; copper(II) sulfate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2016.08.038