5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide

Base Information

• Chemical Name: 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide
• CAS No.: 947540-87-6
• Molecular Formula: C₁₆H₁₂F₃N₃OS
• Molecular Weight: 351.352
• Mol file: 947540-87-6.mol

Synonyms:

Chemical Property of 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide

There total 9 articles about 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide 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:

5-acetyl-thiophene-2-carboxylic acid ethyl ester (33148-82-2) → 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide (947540-87-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium ethanolate / toluene / 0.5 h / 30 °C

1.2: 19 h / 20 - 40 °C

2.1: acetic acid / ethanol / 16 h / 75 °C

3.1: sodium hydroxide; water / 1,4-dioxane / 16 h / 20 °C

4.1: N,N-dimethyl-formamide; oxalyl dichloride / toluene / 2 h

5.1: triethylamine / 0.25 h / 0 - 5 °C

With oxalyl dichloride; water; sodium ethanolate; acetic acid; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; In 1,4-dioxane; ethanol; toluene; 1.1: |Claisen Condensation / 1.2: |Claisen Condensation;

DOI:10.1021/acschemneuro.7b00282

Reference yield:

5-trifluoromethyl-3-hydroxy-1-methylpyrazole (119022-51-4) → 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide (947540-87-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 0.08 h / -10 °C / Inert atmosphere

1.2: 1.28 h / -10 - 20 °C / Inert atmosphere

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium phosphate / 1,4-dioxane / 14 h / 100 °C / High pressure; Inert atmosphere

3.1: 2,2,6,6-tetramethylpiperidine; n-butyllithium / tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

3.2: 1 h / 20 °C

4.1: N,N-dimethyl-formamide; oxalyl dichloride / toluene / 2 h

5.1: triethylamine / 0.25 h / 0 - 5 °C

With potassium phosphate; n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; oxalyl dichloride; 2,2,6,6-tetramethylpiperidine; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; toluene; 2.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acschemneuro.7b00282

Reference yield:

ethyl 5-(4,4,4-trifluoro-3-oxobutanoyl)thiophene-2-carboxylate (679396-71-5) → 5-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yl)-thiophene-2-carboxylic acid phenylamide (947540-87-6)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid / ethanol / 16 h / 75 °C

2: sodium hydroxide; water / 1,4-dioxane / 16 h / 20 °C

3: N,N-dimethyl-formamide; oxalyl dichloride / toluene / 2 h

4: triethylamine / 0.25 h / 0 - 5 °C

With oxalyl dichloride; water; acetic acid; triethylamine; N,N-dimethyl-formamide; sodium hydroxide; In 1,4-dioxane; ethanol; toluene;

DOI:10.1021/acschemneuro.7b00282

upstream raw materials:

5-acetyl-thiophene-2-carboxylic acid ethyl ester

5-trifluoromethyl-3-hydroxy-1-methylpyrazole

ethyl 5-(4,4,4-trifluoro-3-oxobutanoyl)thiophene-2-carboxylate

1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl trifluoromethanesulfonate