methyl 5-methoxy-2-methyl-1H-indole-3-acetate

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Products Intro: Product Name:methyl 5-methoxy-2-methyl-1H-indole-3-acetate
CAS:7588-36-5
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methyl 5-methoxy-2-methyl-1H-indole-3-acetate Basic information
Product Name:methyl 5-methoxy-2-methyl-1H-indole-3-acetate
Synonyms:5-Methoxy-2-Methyl-;methyl 5-methoxy-2-methyl-1H-indole-3-acetate;5-Methoxy-2-methyl-1H-indole-3-acetic acid methyl ester;Methyl 5-Methoxy-2-methylindole-3-acetate;Einecs 231-497-4;1H-Indole-3-acetic acid,5-methoxy-2-methyl-,methyl ester;ZIDO-001;Eethyl 5-methoxy-2-methyl-1H-indole-3-acetate
CAS:7588-36-5
MF:C13H15NO3
MW:233.26
EINECS:231-497-4
Product Categories:Aromatics;Indole Derivatives;Intermediates
Mol File:7588-36-5.mol
methyl 5-methoxy-2-methyl-1H-indole-3-acetate Structure
methyl 5-methoxy-2-methyl-1H-indole-3-acetate Chemical Properties
Melting point 65-68°C
storage temp. Sealed in dry,Room Temperature
solubility Chloroform, Ethyl Acetate, Methanol
form Solid
color Beige
InChIInChI=1S/C13H15NO3/c1-8-10(7-13(15)17-3)11-6-9(16-2)4-5-12(11)14-8/h4-6,14H,7H2,1-3H3
InChIKeyJYUNCKSXPPDNRM-UHFFFAOYSA-N
SMILESN1C2=C(C=C(OC)C=C2)C(CC(OC)=O)=C1C
Safety Information
MSDS Information
methyl 5-methoxy-2-methyl-1H-indole-3-acetate Usage And Synthesis
Chemical PropertiesBrown Solid
UsesIntermediate in the preparation of Indomethacin
Synthesis
Methanol

67-56-1

5-METHOXY-2-METHYL-3-INDOLEACETIC ACID

2882-15-7

methyl 5-methoxy-2-methyl-1H-indole-3-acetate

7588-36-5

General method: 5-methoxy-2-methyl-3-indoleacetic acid (1 eq.) was dissolved with BOP-Cl (1 eq.) in anhydrous CH2Cl2 (3 mL/mmol), triethylamine (2 eq.) was added, and the reaction was carried out for 5 min at room temperature. Subsequently, anhydrous methanol (0.14 mL/mmol) was added and stirred overnight at room temperature. After completion of the reaction, the reaction mixture was diluted with dichloromethane (12 mL/mmol), washed with water (2 x 6 mL/mmol), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure, and the resulting crude product was purified by rapid chromatography on silica gel (gradient elution with ethyl acetate/hexane) to afford methyl 5-methoxy-2-methyl-1H-indole-3-acetate, which was initially a yellow viscous oil, and crystallized and solidified after inoculation and refrigeration.

References[1] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058,10
[2] Tetrahedron, 2012, vol. 68, # 48, p. 10049 - 10058
[3] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 3, p. 1202 - 1218
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 15, p. 4830 - 4837
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1810 - 1827
methyl 5-methoxy-2-methyl-1H-indole-3-acetate Preparation Products And Raw materials
Raw materialsDichloromethane-->Triethylamine-->5-METHOXY-2-METHYL-3-INDOLEACETIC ACID-->Methanol
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