Methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

Base Information

• Chemical Name: Methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate
• CAS No.: 1601-18-9
• Molecular Formula: C20H18ClNO4
• Molecular Weight: 371.82
• Hs Code.: 2933990090
• European Community (EC) Number: 216-494-8
• UNII: V7N8G32K46
• DSSTox Substance ID: DTXSID30166800
• Nikkaji Number: J125.910E
• Wikidata: Q72489152
• Pharos Ligand ID: 5ARWNU3FV8NS
• ChEMBL ID: CHEMBL73572
• Mol file: 1601-18-9.mol

Synonyms:1601-18-9;Indomethacin Methyl Ester;Methyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate;Methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate;methyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate;1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, methyl ester;INDOLE-3-ACETIC ACID, 1-(p-CHLOROBENZOYL)-5-METHOXY-2-METHYL-, METHYL ESTER;EINECS 216-494-8;BRN 0496619;C20H18ClNO4;CHEMBL73572;1-(p-Chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetic acid methyl ester;Indomethacin, methyl ester;DL-OrnithineHCl;Methyl [1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate (Indomethacin Methyl Ester);Indometacin methylester;Indomethacin derivative, 5;1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic Acid Methyl Ester;Indomethacine, methyl ester;Indomethacin, methyl deriv.;Methyl ester of Indomethacin;SCHEMBL14086813;BDBM22952;DTXSID30166800;V7N8G32K46;MFCD01719291;Indomethacin Impurity H [EP Impurity];DS-15077;LS-82141;CS-0061203;FT-0670346;W17150;J-009676;Methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate;Methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate #;Methyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-ylmethyl]acetate;methyl 2-{1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1H-indol-3-yl}acetate

Chemical Property of Methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

Chemical Property:

• Vapor Pressure: 9.13E-09mmHg at 25°C
• Melting Point: 99-100 °C
• Refractive Index: 1.592
• Boiling Point: 463.4 °C at 760 mmHg
• Flash Point: 234 °C
• PSA: 57.53000
• Density: 1.26 g/cm³
• LogP: 4.01570
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 371.0924357
• Heavy Atom Count: 26
• Complexity: 520

Purity/Quality:

99%, ^*data from raw suppliers

Indomethacin methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)OC
• Uses: Selective COX-2 inhibitor

Technology Process of Methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate

There total 18 articles about Methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate 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: 94.0%

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) + methyl iodide (74-88-4) → indomethacin methyl ester (1601-18-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 40 ℃; for 16h;

Reference yield: 93.0%

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) + temozolomide (85622-93-1) → indomethacin methyl ester (1601-18-9)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 60 ℃; for 6h; Sealed tube;

DOI:10.1002/anie.201911896

Reference yield: 90.0%

[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1) + 2,2-dimethoxy-propane (77-76-9) → indomethacin methyl ester (1601-18-9)

Guidance literature:

With hydrogenchloride; for 2h; Ambient temperature;

DOI:10.1021/jo951410m

upstream raw materials:

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

2,2-dimethoxy-propane

4-chloro-benzoyl chloride

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

Downstream raw materials:

4-chlorobenzoic acid hydrazide

3-[2-{5-((1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)methyl)-1,3,4-oxadiazol-2-ylthio}acetyl]-2H-chromen-2-one

[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid hydrazide

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

Refernces

• 1、 Bhat, Mashooq Ahmad,Mohamed, A. Al-Omar,Mohammad, Raish,Ansari, Mushtaq Ahmad,Abuelizz, Hatem A.,Bakheit, Ahmed H.,Naglah, Ahmed M.. "Indole derivatives as cyclooxygenase inhibitors: Synthesis, biological evaluation and docking studies". . . Retrieved 2018.
• 2、 Fronza,Mele,Redenti,Ventura. "1H NMR and molecular modeling study on the inclusion complex β-cyclodextrin-indomethacin". . p. 909 - 914. Retrieved 1996.
• 3、 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.
• 4、 Chiba, Shunsuke,Li, Haoyu,Liu, Yuliang. "Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis". supporting information. p. 6264 - 6267. Retrieved 2021/07/02.