[4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid

Base Information

Chemical Name:[4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid
CAS No.:1297141-43-5
Molecular Formula:C₂₂H₁₈BClF₄N₄O₄
Molecular Weight:524.667
Hs Code.:

Synonyms:[4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid

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Chemical Property of [4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid

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Technology Process of [4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid

There total 21 articles about [4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic 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: 50.0%

: 1297141-46-8
4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-piperazinon

: 1297141-43-5
[4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid

Guidance literature:: With sodium periodate; ammonium acetate; water; In tetrahydrofuran; acetone; for 24h;

Reference yield:

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

: 1297141-43-5
[4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid

Guidance literature:: Multi-step reaction with 14 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: sodium hydroxide / methanol / 4 h / 50 °C

10.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; N,N-dimethyl-formamide / 1.25 h / 0 °C

11.1: boron tribromide / dichloromethane / 4 h / -78 °C / Cooling with ice bath

12.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

13.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 8.5 h / 100 °C

13.2: 0.17 h / 120 °C / microwave

14.1: sodium periodate; water; ammonium acetate / tetrahydrofuran; acetone / 24 h

With potassium phosphate; sodium periodate; 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; ammonium acetate; water; potassium acetate; boron tribromide; sodium hydride; potassium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; sodium hydroxide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; mineral oil;

Reference yield:

: 458-50-4
1-bromo-2-fluoro-4-methoxybenzene

: 1297141-43-5
[4-(4-{[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-2-oxo-1-piperazinyl)-3-fluorophenyl]boronic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium carbonate / copper(l) iodide; trans-N,N'-dimethyl-1,2-cyclohexyldiamine / 1,4-dioxane / 84 h / 120 °C

2.1: hydrogenchloride / dichloromethane; 1,4-dioxane / 1.5 h

3.1: N-ethyl-N,N-diisopropylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate; N,N-dimethyl-formamide / 1.25 h / 0 °C

4.1: boron tribromide / dichloromethane / 4 h / -78 °C / Cooling with ice bath

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C

6.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 8.5 h / 100 °C

6.2: 0.17 h / 120 °C / microwave

7.1: sodium periodate; water; ammonium acetate / tetrahydrofuran; acetone / 24 h

With hydrogenchloride; sodium periodate; ammonium acetate; water; potassium acetate; boron tribromide; potassium carbonate; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; trans-N,N'-dimethyl-1,2-cyclohexyldiamine; copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone;