{3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester

Base Information

• Chemical Name: {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester
• CAS No.: 1404531-74-3
• Molecular Formula: C₂₆H₂₅ClN₄O₄
• Molecular Weight: 492.962
• Mol file: 1404531-74-3.mol

Synonyms:{3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester

Chemical Property of {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester

There total 17 articles about {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid 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: 67.0%

1-[1-(4-aminophenyl)-5-methyl-1H-pyrazol-4-yl]butan-1-one (1404530-78-4) + 5-chloro-1-(2-methoxy-2-oxoethyl)-1H-indole-3-carboxylic acid (1404530-50-2) → {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester (1404531-74-3)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,2-dichloro-ethane; at 20 ℃; for 20h;

DOI:10.1021/jm500588w

Reference yield:

5-methyl-1-(4-nitrophenyl)-1H-pyrazole-4-carboxylic acid → {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester (1404531-74-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 20 h / 20 °C

1.2: 16 h / 45 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 24 h / 20 °C

3.1: hydrogenchloride; water / 2 h / 105 °C / Reflux

3.2: 0 °C

4.1: cyclohexene / palladium on activated charcoal / ethanol / 4 h / Inert atmosphere; Reflux

5.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 h / 20 °C

With hydrogenchloride; dmap; water; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1,1'-carbonyldiimidazole; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; mineral oil;

Reference yield:

ethyl 3-[5-methyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]-3-oxopropanoate (1404530-79-5) → {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-chloro-indol-1-yl}acetic acid methyl ester (1404531-74-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: 24 h / 20 °C

2.1: hydrogenchloride; water / 2 h / 105 °C / Reflux

2.2: 0 °C

3.1: cyclohexene / palladium on activated charcoal / ethanol / 4 h / Inert atmosphere; Reflux

4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane / 20 h / 20 °C

With hydrogenchloride; dmap; water; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; mineral oil;

upstream raw materials:

5-chloro-1H-indole-3-carboxylic acid

1-[1-(4-aminophenyl)-5-methyl-1H-pyrazol-4-yl]butan-1-one

5-chloro-1-(2-methoxy-2-oxoethyl)-1H-indole-3-carboxylic acid

ethyl 3-[5-methyl-1-(4-nitrophenyl)-1H-pyrazol-4-yl]-3-oxopropanoate

Downstream raw materials:

C₃₁H₃₃ClN₆O₅

N-[4-(4-butyryl-5-methyl-1H-pyrazol-1-yl)phenyl]-5-chloro-1-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]-1H-indole-3-carboxamide

[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenyl]-5-chloro-1-{2-[4-(5-methylisoxazol-3-ylmethyl)piperazin-1-yl]-2-oxoethyl}-1H-indole-3-carboxamide hydrochloride

[4-(4-butyryl-5-methylpyrazol-1-yl)phenyl]-5-chloro-1-{2-[4-(2-hydroxyethyl)piperazin-1-yl]-2-oxoethyl}-1H-indole-3-carboxamide hydrochloride