5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

Base Information

Chemical Name:5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide
CAS No.:1378868-65-5
Molecular Formula:C₃₃H₃₅BF₄N₄O₆S
Molecular Weight:702.535
Hs Code.:

5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

Synonyms:5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

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Chemical Property of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

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Technology Process of 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

There total 15 articles about 5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide 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: 94.0%

: 6-(N-(4-bromo-3-(trifluoromethoxy)benzyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide

: 73183-34-3
bis(pinacol)diborane

: 1378868-65-5
5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

Guidance literature:: With potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 100 ℃; Inert atmosphere;

Reference yield:

: 403-43-0
4-fluorobenzoyl chloride

: 1378868-65-5
5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine; magnesium chloride / acetonitrile / 2 h / Cooling with ice-salt bath

1.2: 20 °C / Cooling with ice-salt bath

1.3: 1.5 h / Cooling with ice

2.1: trifluoromethylsulfonic anhydride; triethylamine; Triphenylphosphine oxide / 1,2-dichloro-ethane / 2 h / 85 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

4.1: potassium hydroxide; water / ethanol / 1 h / 85 °C

5.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 21 °C / Inert atmosphere

5.2: 0.5 h / 20 °C / Inert atmosphere

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

With trifluoromethylsulfonic anhydride; water; potassium acetate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; Triphenylphosphine oxide; potassium hydroxide; magnesium chloride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

: 13091-23-1
4-chloro-3-nitropyridine

: 1378868-65-5
5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethoxy)benzyl)methylsulfonamido)pyrazolo[1,5-a]pyridine-3-carboxamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: potassium fluoride; sodium bromide / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / Inert atmosphere; Reflux

2.1: hydrogen / palladium on activated charcoal / methanol / 20 °C / 2585.81 Torr

3.1: triethylamine / dichloromethane / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 °C

5.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

6.1: 72 h / 20 °C / Inert atmosphere

7.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 100 °C / Inert atmosphere

8.1: potassium hydroxide; water / ethanol / 1 h / 85 °C

9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.25 h / 21 °C / Inert atmosphere

9.2: 0.5 h / 20 °C / Inert atmosphere

10.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 100 °C / Inert atmosphere

With potassium fluoride; tetrabutyl ammonium fluoride; water; hydrogen; potassium acetate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; sodium bromide; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;