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

Melting point:

99-100 °C

Boiling point:

463.4±45.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)

form 

Solid

color 

Pale Yellow to Light Green

NIST Chemistry Reference

Indomethacin, methyl ester(1601-18-9)

methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate Usage And Synthesis

Chemical Properties

Pale Green Solid

Uses

Selective COX-2 inhibitor

Synthesis

GENERAL METHOD: 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetic acid (1 eq.) and BOP-Cl (1 eq.) were suspended in dichloromethane (20 mL/g of acid), triethylamine (2 eq.) was added slowly and the mixture was stirred for 10 minutes. Methanol (4 eq.) was then added and the reaction mixture continued to be stirred for at least 12 hours. Upon completion of the reaction, the solvent was removed by evaporation and the resulting solid was purified by column chromatography with the eluent being a solvent mixture of hexane and ethyl acetate (3:1, v/v) at a boiling range of 80-100°C. Finally, the solvent was removed under reduced pressure to give methyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate as a light yellow solid.

References

[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 15, p. 4830 - 4837
[2] Pharmazie, 2003, vol. 58, # 2, p. 99 - 103
[3] Patent: CN105418480, 2016, A. Location in patent: Paragraph 0031
[4] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 3, p. 745 - 762
[5] European Journal of Pharmaceutical Sciences, 2001, vol. 14, # 4, p. 301 - 311

methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate(1601-18-9)Related Product Information

• Methanone, (4-chlorophenyl)[2,6-dichloro-4-(hydroxymethyl)phenyl]-
• Indometacin Impurity 17
• Indomethacin-d4
• Indometacin
• 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, ethyl ester
• 4-Chloro-2-(4-chlorobenzoyl)-1-(4-Methoxyphenyl)hydrazide Benzoic Acid
• 4-Chloro-N-(4-Methoxyphenyl)benzaMide, 97%
• IndoMethacin DiaMide
• 2-(4-METHOXYPHENYL)HYDRAZINESULFONIC ACID SODIUM SALT MONOHYDRATE
• 5-METHOXY-2-METHYL-3-INDOLEACETIC ACID
• 4-Chlorobenzoic acid
• Indometacin EP Impurity G
• 1H-INDOLE-3-ACETICACID,1-(3-CHLOROBENZOYL)-5-METHOXY-2-METHYL
• Indometacin Impurity 16
• Benzoic acid, 4-chloro-, 2,3-dihydroxypropyl ester
• 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, 2-hydroxypropyl ester
• 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-,2,3-d ihydroxypropyl ester
• Indometacin Impurity 18