6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide

Base Information

• Chemical Name: 6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide
• CAS No.: 1378869-30-7
• Molecular Formula: C₂₇H₂₂BrClF₄N₄O₃S
• Molecular Weight: 673.913
• Mol file: 1378869-30-7.mol

Synonyms:6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide

Chemical Property of 6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide

There total 17 articles about 6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[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:

2-fluoro-3-(trifluoromethyl)aniline (123973-25-1) → 6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide (1378869-30-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 15 - 20 °C / Inert atmosphere

2.1: triethylamine / palladium diacetate; 1,1'-bis-(diphenylphosphino)ferrocene / dimethyl sulfoxide / 16 h / 80 °C / 37503.8 Torr

3.1: hydrogen bromide / acetonitrile; water / 0.17 h / 0 °C

3.2: 1.08 h / 0 °C

3.3: 1.5 h / 0 - 70 °C

4.1: diisobutylaluminium hydride / toluene / 1 h / -78 - 0 °C

4.2: -78 °C

5.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 0.5 h / -10 - 20 °C / Inert atmosphere

6.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With N-Bromosuccinimide; hydrogen bromide; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; potassium iodide; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile;

Reference yield:

4-chloro-3-nitropyridine (13091-23-1) → 6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide (1378869-30-7)

Guidance literature:

Multi-step reaction with 11 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 / 0.5 h / 80 °C / Inert atmosphere

6.1: dichloromethane / 48 h / 20 °C / Inert atmosphere

7.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 100 °C / Inert atmosphere

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

8.2: pH 2

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: trifluoroacetic acid / 1 h / Reflux

11.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With potassium fluoride; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; potassium iodide; sodium bromide; potassium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

para-chlorobenzoic acid (74-11-3) → 6-(N-(4-bromo-3-fluoro-2-(trifluoromethyl)benzyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylpyrazolo[1,5-a]pyridine-3-carboxamide (1378869-30-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: oxalyl dichloride / N,N-dimethyl-formamide / dichloromethane / 2 h / Reflux

2.1: triethylamine; magnesium chloride / acetonitrile / 3 h / Cooling with ice-salt bath

2.2: 20 °C / Cooling with ice-salt bath

2.3: 1.5 h / Cooling with ice

3.1: trifluoromethylsulfonic anhydride; triethylamine; Triphenylphosphine oxide / 1,2-dichloro-ethane / 1.5 h / 85 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 100 °C / Inert atmosphere

5.1: potassium hydroxide; water / ethanol / 1 h / 85 °C / Inert atmosphere

5.2: pH 2

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

6.2: 0.5 h / 20 °C / Inert atmosphere

7.1: trifluoroacetic acid / 1 h / Reflux

8.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

With oxalyl dichloride; trifluoromethylsulfonic anhydride; water; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; Triphenylphosphine oxide; potassium iodide; potassium hydroxide; magnesium chloride; N,N-dimethyl-formamide; In ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

4-chloro-benzoyl chloride

2-fluoro-3-(trifluoromethyl)aniline

para-chlorobenzoic acid

4-chloro-3-nitropyridine

Downstream raw materials:

(4-((N-(2-(4-chlorophenyl)-5-cyclopropyl-3-(methylcarbamoyl)pyrazolo[1,5-a]pyridin-6-yl)methylsulfonamido)methyl)-2-fluoro-3-(trifluoromethyl)phenyl)boronic acid

Refernces