ChemicalBook--->CAS DataBase List--->7588-36-5

7588-36-5

7588-36-5 Structure

7588-36-5 Structure
IdentificationBack Directory
[Name]

methyl 5-methoxy-2-methyl-1H-indole-3-acetate
[CAS]

7588-36-5
[Synonyms]

ZIDO-001
Einecs 231-497-4
5-Methoxy-2-Methyl-
Methyl 5-Methoxy-2-methylindole-3-acetate
Eethyl 5-methoxy-2-methyl-1H-indole-3-acetate
methyl 5-methoxy-2-methyl-1H-indole-3-acetate
5-Methoxy-2-methyl-1H-indole-3-acetic acid methyl ester
1H-Indole-3-acetic acid,5-methoxy-2-methyl-,methyl ester
[EINECS(EC#)]

231-497-4
[Molecular Formula]

C13H15NO3
[MOL File]

7588-36-5.mol
[Molecular Weight]

233.26
Chemical PropertiesBack Directory
[Melting point ]

65-68°C
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

Chloroform, Ethyl Acetate, Methanol
[form ]

Solid
[color ]

Beige
[InChI]

InChI=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
[InChIKey]

JYUNCKSXPPDNRM-UHFFFAOYSA-N
[SMILES]

N1C2=C(C=C(OC)C=C2)C(CC(OC)=O)=C1C
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H317
[Precautionary statements ]

P280
Hazard InformationBack Directory
[Chemical Properties]

Brown Solid
[Uses]

Intermediate 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
Spectrum DetailBack Directory
[Spectrum Detail]

methyl 5-methoxy-2-methyl-1H-indole-3-acetate(7588-36-5)1HNMR
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