Multi-step reaction with 6 steps
1.1: hydrogen bromide / 1,4-dioxane / 17.5 h / 20 °C
2.1: 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 / 1 h / 20 °C
3.1: ammonium acetate / 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 140 °C / Microwave irradiation
4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C
4.2: 14 h / 20 °C
5.1: tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 24 h / 80 °C / Inert atmosphere
6.1: trifluoroacetic acid / dichloromethane / 10 h / 20 °C
With
tetrakis(triphenylphosphine) palladium(0); ammonium acetate; hydrogen bromide; sodium hydride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
In
1,4-dioxane; 1,2-dimethoxyethane; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
5.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/jm401836p