5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

Base Information

Chemical Name:5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid
CAS No.:1297141-01-5
Molecular Formula:C₁₃H₁₁F₃N₂O₃
Molecular Weight:300.237
Hs Code.:

Synonyms:5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

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Chemical Property of 5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

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Technology Process of 5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

There total 17 articles about 5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

: 1297140-99-8
methyl 5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylate

: 1297141-01-5
5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

Guidance literature:: methyl 5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylate; With water; lithium hydroxide; In tetrahydrofuran; methanol; for 2h;

With hydrogenchloride; In water; pH=3;

Reference yield:

: 170886-13-2
4-hydroxy-2-trifluoromethylpyridine

: 1297141-01-5
5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 °C

1.2: 3 h / 5 - 20 °C

2.1: dichloromethane / 20 °C

2.2: Cooling

3.1: potassium carbonate / N,N-dimethyl-formamide / 5 - 20 °C

4.1: sulfuric acid / 2 h / 90 °C

4.2: 90 °C

5.1: sulfuric acid / Reflux

5.2: 90 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C

7.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere

8.1: 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

9.1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / hexane / 80 °C / Inert atmosphere

10.1: sulfuric acid; dihydrogen peroxide / water; tetrahydrofuran / 2 h / 0 - 50 °C

11.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C

12.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h

12.2: pH 3

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; water; dihydrogen peroxide; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; sulfuric acid; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

Reference yield:

: 1297137-35-9
3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

: 1297141-01-5
5-cyclopropyl-3-(methyloxy)-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 °C

2.2: 3 h / 5 - 20 °C

3.1: dichloromethane / 20 °C

3.2: Cooling

4.1: potassium carbonate / N,N-dimethyl-formamide / 5 - 20 °C

5.1: sulfuric acid / 2 h / 90 °C

5.2: 90 °C

6.1: sulfuric acid / Reflux

6.2: 90 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 10 h / 20 °C

8.1: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 4.5 h / 90 °C / Inert atmosphere

9.1: 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

10.1: 4,4'-di-tert-butyl-2,2'-bipyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / hexane / 80 °C / Inert atmosphere

11.1: sulfuric acid; dihydrogen peroxide / water; tetrahydrofuran / 2 h / 0 - 50 °C

12.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 50 °C

13.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h

13.2: pH 3

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; water; dihydrogen peroxide; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; lithium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; sulfuric acid; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;