Multi-step reaction with 9 steps
1.1: sulfuric acid / 2 h / 90 °C
1.2: 90 °C
2.1: sulfuric acid / Reflux
2.2: 90 °C
3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C
4.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere
5.1: 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one / N,N-dimethyl-formamide / 1 h / 60 °C
6.1: sodium hydroxide / methanol / 4 h / 50 °C
7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C
8.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 65 °C
9.1: dichloromethane / 20 °C
With
potassium phosphate; sulfuric acid; 3-(1-{[3,4-dichloro-5-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-yl]carbonyl}-4-piperidinyl)-1,3-oxazolidin-2-one; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide;
dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sulfuric acid;
In
1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide;