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

Base Information

• Chemical Name: {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-bromo-indol-1-yl}acetic acid methyl ester
• CAS No.: 1404532-70-2
• Molecular Formula: C₂₆H₂₅BrN₄O₄
• Molecular Weight: 537.413
• Mol file: 1404532-70-2.mol

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

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

There total 18 articles about {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-bromo-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: 81.0%

1-[1-(4-aminophenyl)-5-methyl-1H-pyrazol-4-yl]butan-1-one (1404530-78-4) + 5-bromo-1-(2-methoxy-2-oxoethyl)-1H-indole-3-carboxylic acid (1404532-12-2) → {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-bromo-indol-1-yl}acetic acid methyl ester (1404532-70-2)

Guidance literature:

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

DOI:10.1021/jm500588w

Reference yield:

5-bromo-1H-indole (10075-50-0) → {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-bromo-indol-1-yl}acetic acid methyl ester (1404532-70-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diethyl ether / 2 h / -5 °C

2.1: potassium hydroxide / water / 4 h / Reflux

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / -10 - 20 °C

3.2: 20 °C

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

With dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; In diethyl ether; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm500588w

Reference yield:

methyl 5-methyl-1H-pyrazole-4-carboxylate → {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-bromo-indol-1-yl}acetic acid methyl ester (1404532-70-2)

Guidance literature:

Multi-step reaction with 8 steps

1: potassium carbonate / N,N-dimethyl-formamide / 120 h / 20 °C

2: potassium hydroxide; water / ethanol / 6 h / Reflux

3: dmap; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride / dichloromethane / 1 h / 20 °C

4: diethyl ether; tetrahydrofuran / 4 h / -30 - 20 °C

5: hydrogenchloride / water; 1,4-dioxane / 6 h

6: sodium hydride / N,N-dimethyl-formamide; mineral oil / 16 h / 20 °C

7: palladium 10% on activated carbon / ethanol; cyclohexane / 4 h / Inert atmosphere; Reflux

8: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / 1,2-dichloro-ethane / 20 °C

With hydrogenchloride; dmap; palladium 10% on activated carbon; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; cyclohexane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jm500588w

upstream raw materials:

5-bromo-1H-indole

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

1-(5-bromo-1H-indol-3-yl)-2,2,2-trifluoroethanone

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

Downstream raw materials:

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

methyl (3-{[4-(4-butyryl-5-methyl-1H-pyrazol-1-yl)phenyl]carbamoyl}-5-phenyl-1H-indol-1-yl)acetate

sodium {3-[4-(4-butyryl-5-methyl-pyrazol-1-yl)phenylcarbamoyl]-5-cyano-indol-1-yl}acetate

C₃₁H₃₃N₇O₃*ClH