3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide

Base Information

• Chemical Name: 3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide
• CAS No.: 1427400-25-6
• Molecular Formula: C₁₆H₁₁F₄N₅O
• Molecular Weight: 365.29
• Mol file: 1427400-25-6.mol

Synonyms:

Chemical Property of 3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide

There total 5 articles about 3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide 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:

3-nitro-5-trifluoromethyl-pyridine-2-carbonitrile (866775-16-8) → 3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide (1427400-25-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 18 h

1.2: 24 h / Reflux

1.3: 84 h / Reflux

2.1: sulfuric acid; bromine / water; acetic acid / 18 h / 20 °C

3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / tetrahydrofuran / 0.25 h / 160 °C / Inert atmosphere; Microwave irradiation

4.1: water; sodium hydroxide / ethanol / 0.25 h / 20 °C

5.1: triethylamine; HATU / 1-methyl-pyrrolidin-2-one / 20 - 100 °C / Sealed tube; Microwave irradiation

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sulfuric acid; palladium 10% on activated carbon; water; hydrogen; bromine; caesium carbonate; triethylamine; HATU; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; water; acetic acid; ethyl acetate;

Reference yield:

3-amino-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (866775-17-9) → 3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide (1427400-25-6)

Guidance literature:

Multi-step reaction with 4 steps

1: sulfuric acid; bromine / water; acetic acid / 18 h / 20 °C

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / tetrahydrofuran / 0.25 h / 160 °C / Inert atmosphere; Microwave irradiation

3: water; sodium hydroxide / ethanol / 0.25 h / 20 °C

4: triethylamine; HATU / 1-methyl-pyrrolidin-2-one / 20 - 100 °C / Sealed tube; Microwave irradiation

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sulfuric acid; water; bromine; caesium carbonate; triethylamine; HATU; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol; water; acetic acid;

Reference yield:

3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (866775-18-0) → 3-amino-6-(4-fluorophenyl)-N-(1H-pyrazol-3-yl)-5-(trifluoromethyl)picolinamide (1427400-25-6)

Guidance literature:

Multi-step reaction with 3 steps

1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / tetrahydrofuran / 0.25 h / 160 °C / Inert atmosphere; Microwave irradiation

2: water; sodium hydroxide / ethanol / 0.25 h / 20 °C

3: triethylamine; HATU / 1-methyl-pyrrolidin-2-one / 20 - 100 °C / Sealed tube; Microwave irradiation

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; caesium carbonate; triethylamine; HATU; sodium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol;

upstream raw materials:

3-amino-6-(2,6-difluorophenyl)-5-trifluoromethyl-2-pyridinecarboxylicacid

3-nitro-5-trifluoromethyl-pyridine-2-carbonitrile

3-amino-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

3-amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester

Refernces