Indomethacin ethyl ester

Base Information

• Chemical Name: Indomethacin ethyl ester
• CAS No.: 16401-99-3
• Molecular Formula: C21H20 Cl N O4
• Molecular Weight: 385.847
• UNII: 8AON0U1UBT
• DSSTox Substance ID: DTXSID50167697
• Nikkaji Number: J381.491B
• Wikidata: Q83037123
• Pharos Ligand ID: 5TMX1P4YDULU
• ChEMBL ID: CHEMBL328864
• Mol file: 16401-99-3.mol

Synonyms:indomethacin ethyl ester

Chemical Property of Indomethacin ethyl ester

Chemical Property:

• Vapor Pressure: 3.35E-09mmHg at 25°C
• Melting Point: 95-96 °C
• Boiling Point: 475.3°Cat760mmHg
• Flash Point: 241.3°C
• PSA: 57.53000
• Density: 1.24g/cm³
• LogP: 4.40580
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 385.1080858
• Heavy Atom Count: 27
• Complexity: 534

Purity/Quality:

98% ^*data from raw suppliers

IndomethacinEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC1=C(N(C2=C1C=C(C=C2)OC)C(=O)C3=CC=C(C=C3)Cl)C
• Uses: Indomethacin Ethyl Ester (Indomethacin EP Impurity I) is the ethyl ester of the nonsteroidal anti-inflammatory drug Indomethacin (I641000). Indomethacin Ethyl Ester is a selective COX-2 inhibitor and is used (along with Indomethacin) as loaded nanocapsules as anticancer treatment showing a decrease in glioma cell proliferation.

Technology Process of Indomethacin ethyl ester

There total 9 articles about Indomethacin 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: 97.0%

ethanol (64-17-5) + [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) → indomethacin ethyl ester (16401-99-3)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acs.orglett.8b03476

Reference yield: 90.0%

4-chloro-benzoyl chloride (122-01-0) + ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate (17536-38-8) → indomethacin ethyl ester (16401-99-3)

Guidance literature:

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 1h;

4-chloro-benzoyl chloride; In tetrahydrofuran; for 3h;

DOI:10.1016/j.tetlet.2013.11.065

Reference yield: 67.0%

→ indomethacin methyl ester + indomethacin ethyl ester (16401-99-3)

Guidance literature:

upstream raw materials:

4-chloro-benzoyl chloride

ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate

chloroformic acid ethyl ester

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

Downstream raw materials:

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid

N₁-[2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetyl]-N₄-cyclohexyl thiosemicarbazide

N₁-[2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetyl]-N₄-n-butyl thiosemicarbazide

Refernces

• 1、 Cheng, Xionglve,Jiang, Gangzhong,Li, Xingxing,Tao, Suyan,Wan, Xiaobing,Zhao, Yanwei,Zheng, Yonggao. "Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite". supporting information. p. 2713 - 2718. Retrieved 2021/06/25.
• 2、 Svec, Riley L.,Hergenrother, Paul J.. "Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations". supporting information. p. 1857 - 1862. Retrieved 2019/12/27.