2-Thiophenecarboxylic acid, 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester

Base Information

• Chemical Name: 2-Thiophenecarboxylic acid, 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester
• CAS No.: 1047630-52-3
• Molecular Formula: C10H9ClN2O2S
• Molecular Weight: 256.71
• Mol file: 1047630-52-3.mol

Synonyms:2-Thiophenecarboxylic acid, 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester;methyl 5-chloro-4-(1-methylpyrazol-5-yl)-2-thiophenecarboxylate;methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

Chemical Property of 2-Thiophenecarboxylic acid, 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester

Chemical Property:

• PSA: 72.36000
• LogP: 2.58860

Purity/Quality:

98%min ^*data from raw suppliers

Methyl5-Chloro-4-(1-methylpyrazol-5-yl)-2-thiophenecarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Thiophenecarboxylic acid, 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester

There total 5 articles about 2-Thiophenecarboxylic acid, 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester 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: 70.0%

methyl 4-bromo-5-chlorothiophene-2-carboxylate (1047630-72-7) + 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (847818-74-0) → methyl 5-chloro-4-(1-methylpyrazol-5-yl)-2-thiophenecarboxylate (1047630-52-3)

Guidance literature:

With potassium carbonate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In 1,4-dioxane; water; at 75 ℃; for 1.5h;

Reference yield: 24.0%

methyl 5-chloro-4-iodo-2-thiophenecarboxylate (1047644-88-1) + 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole (1044851-76-4) → methyl 5-chloro-4-(1-methylpyrazol-5-yl)-2-thiophenecarboxylate (1047630-52-3)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; water; at 80 ℃; for 15h;

Reference yield:

5-Chlorothiophene-2-carboxylic acid (24065-33-6) → methyl 5-chloro-4-(1-methylpyrazol-5-yl)-2-thiophenecarboxylate (1047630-52-3)

Guidance literature:

Multi-step reaction with 3 steps

1: sulfuric acid / 53 °C

2: N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride / acetic acid / 70 °C

3: C₂₄H₅₄P₂Pd; potassium carbonate / 1,4-dioxane; water / 70 °C

With sulfuric acid; C₂₄H₅₄P₂Pd; potassium carbonate; N,N,N-trimethylbenzenemethanaminium dichloroiodate; zinc(II) chloride; In 1,4-dioxane; water; acetic acid;

DOI:10.1358/dof.2014.039.08.2177902

upstream raw materials:

methyl 4-bromo-5-chlorothiophene-2-carboxylate

1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole

methyl 5-chloro-4-iodo-2-thiophenecarboxylate

5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1-methyl-1H-pyrazole

Downstream raw materials:

5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylic acid

5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid

5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-{(1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}-2-thiophenecarboxamide

N-{(1S)-2-amino-1-[(3-fluorophenyl)methyl] ethyl}-5-chloro-4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

Refernces

• 1、 -. "INHIBITORS OF AKT ACTIVITY". Page/Page column 188-189. . Retrieved 2008/12/08.