1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester
• CAS No.: 850554-40-4
• Molecular Formula: C₂₉H₃₄Cl₂N₂O₄
• Molecular Weight: 545.506
• Mol file: 850554-40-4.mol

Synonyms:1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester

Chemical Property of 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester

There total 7 articles about 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl 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: 75.0%

5-<2'-(tetrahydropyranyloxy)>-1-pentene (64841-44-7) + 5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (183232-62-4) → 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester (850554-40-4)

Guidance literature:

5-<2'-(tetrahydropyranyloxy)>-1-pentene; With 9-borabicyclo[3.3.1]nonane dimer; at 23 ℃; for 16h;

5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester; With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In 1,4-dioxane; at 120 ℃; for 60h;

DOI:10.1016/j.tetlet.2005.01.165

Reference yield:

ethyl 4-(4-bromophenyl)-3-methyl-2,4-dioxobutanoate lithium salt → 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester (850554-40-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 72 percent / ethanol / 16 h / 23 °C

2.1: 99 percent / AcOH / 48 h / Heating

3.1: 9-BBN / 16 h / 23 °C

3.2: 75 percent / K₃PO₄ / Pd(PPh₃)4 / dioxane / 60 h / 120 °C

With 9-borabicyclo[3.3.1]nonane dimer; acetic acid; In ethanol; 3.2: Suzuki coupling;

DOI:10.1016/j.tetlet.2005.01.165

Reference yield:

4'-Bromopropiophenone (10342-83-3) → 1-(2,4-dichloro-phenyl)-4-methyl-5-{4-[5-(tetrahydro-pyran-2-yloxy)-pentyl]-phenyl}-1H-pyrazole-3-carboxylic acid ethyl ester (850554-40-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LiN(SiMe₃)2 / diethyl ether / 0.75 h / 23 °C

1.2: 97 percent / diethyl ether / 16 h / 23 °C

2.1: 72 percent / ethanol / 16 h / 23 °C

3.1: 99 percent / AcOH / 48 h / Heating

4.1: 9-BBN / 16 h / 23 °C

4.2: 75 percent / K₃PO₄ / Pd(PPh₃)4 / dioxane / 60 h / 120 °C

With 9-borabicyclo[3.3.1]nonane dimer; acetic acid; lithium hexamethyldisilazane; In diethyl ether; ethanol; 4.2: Suzuki coupling;

DOI:10.1016/j.tetlet.2005.01.165

upstream raw materials:

5-<2'-(tetrahydropyranyloxy)>-1-pentene

5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid ethyl ester

4-(4-bromo-phenyl)-2-[(2,4-dichloro-phenyl)-hydrazono]-3-methyl-4-oxo-butyric acid ethyl ester

3,4-dihydro-2H-pyran

Downstream raw materials:

N-(piperidin-1-yl)-1-(2,4-dichlorophenyl)-5-{4-(5-hydroxypentyl)phenyl}-4-methyl-1H-pyrazole-3-carboxamide

5-[4-(5-azido-pentyl)-phenyl]-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide

methanesulfonic acid 5-{4-[2-(2,4-dichloro-phenyl)-4-methyl-5-(piperidin-1-ylcarbamoyl)-2H-pyrazol-3-yl]-phenyl}-pentyl ester