Multi-step reaction with 9 steps
1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 20 °C
2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; (Rc,Sp)-Duanphos / methanol / 3 h / 20 °C / 3345.86 Torr / Inert atmosphere
3.1: lithium hydroxide; water / tetrahydrofuran; water / 20 °C / pH 3 / Inert atmosphere
4.1: 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 / 20 °C
4.2: 20 °C
5.1: lithium hydroxide / dichloromethane; trifluoroacetic acid / 20 °C
5.2: 4 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Reflux
7.1: hydrogenchloride / 1,4-dioxane
8.1: triethylamine / dichloromethane / 20 °C
9.1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); ruphos / 100 °C / Heating; Sealed tube
With
hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); lithium aluminium tetrahydride; (Rc,Sp)-Duanphos; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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; lithium hydroxide; sodium t-butanolate; ruphos;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; trifluoroacetic acid;
DOI:10.1021/jm4016735