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1601-18-9

1601-18-9 Structure

1601-18-9 Structure
IdentificationBack Directory
[Name]

methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate
[CAS]

1601-18-9
[Synonyms]

L 588983
Indometacin Impurity H
Indapamide EP Impurity H
Indometacin EP Impurity H
Indomethacin Methyl Ester
Indomethacin EP Impurity H
Methyl 2-(1-(4-chlorobenzoyl)
Methyl [1-(4-Chlorobenzoyl)-5-metho
Indomethacin Impurity 8(Indomethacin EP Impurity H)
Methyl N-(p-Chlorobenzoyl)-2-Methyl-5-Methoxy-3-indolylacetate
methyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetate
methyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate
Methyl [1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetate
Methyl 2-(1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-1H-indol-3-yl)acetate
1-(4-Chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid methyl ester
methyl 2-[1-(4-chlorophenyl)carbonyl-5-methoxy-2-methyl-indol-3-yl]ethanoate
2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl]acetic acid methyl ester
1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, Methyl ester
[1-(4-Chlorobenzoyl)-2-methyl-5-methoxy-1H-indole-3-yl]acetic acid methyl ester
Indomethacin impurity 7/Indomethacin EP Impurity H/methyl 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate
[EINECS(EC#)]

216-494-8
[Molecular Formula]

C20H18ClNO4
[MDL Number]

MFCD01719291
[MOL File]

1601-18-9.mol
[Molecular Weight]

371.81
Chemical PropertiesBack Directory
[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)
Hazard InformationBack Directory
[Chemical Properties]

Pale Green Solid
[Uses]

Selective COX-2 inhibitor
[Synthesis]

Methanol

67-56-1

Indometacin

53-86-1

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

1601-18-9

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
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