Multi-step reaction with 7 steps
1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 8 h / 20 °C
2.1: diethylamine / dichloromethane / 2 h / 20 °C
3.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; sodium hydrogencarbonate / water; methanol / 12 h / 20 °C
4.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C
5.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / dichloromethane / 12 h / 20 °C
6.1: tetrakis(triphenylphosphine) palladium(0); N-methylaniline / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere
7.1: ozone / dichloromethane / 0.08 h / -78 °C
7.2: 2 h / -78 °C
With
imidazole-1-sulfonyl azide hydrochloride; tetrakis(triphenylphosphine) palladium(0); copper(ll) sulfate pentahydrate; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; ozone; acetic acid; diethylamine; N-ethyl-N,N-diisopropylamine; N-methylaniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja4012468