potassium carbonate in N,N-dimethyl-formamide T=65°C; 2 h;

1.1: water; sulfuric acid / 40 h / 90 °C 2.1: ethanethiol; aluminum tri-bromide / 48 h / 20 °C 3.1: sulfuric acid / Reflux 3.2: 90 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C 5.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere 6.1: 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 7.1: sodium hydroxide / methanol / 4 h / 50 °C 8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 9.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 65 °C View Scheme

1.1: ethanethiol; aluminum tri-bromide / 48 h / 20 °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) dichloromethane adduct / 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 View Scheme

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) dichloromethane adduct / 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 View Scheme

1.1: sulfuric acid / Reflux 1.2: 90 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C 3.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere 4.1: 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 5.1: sodium hydroxide / methanol / 4 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 7.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 65 °C View Scheme

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C 2: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere 3: 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 4: sodium hydroxide / methanol / 4 h / 50 °C 5: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 6: potassium carbonate / N,N-dimethyl-formamide / 2 h / 65 °C View Scheme

1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere 2: 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 3: sodium hydroxide / methanol / 4 h / 50 °C 4: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 5: potassium carbonate / N,N-dimethyl-formamide / 2 h / 65 °C View Scheme

tert.-butylhydroperoxide; IPS; zinc sulfinate in chloroform; water T=20 - 50°C; 12 h; Overall yield = 23 percent; regioselective reaction;

1: sodium hydroxide / methanol / 4 h / 50 °C 2: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 2 h / 65 °C View Scheme

1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 65 °C View Scheme