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Methyl 5-methoxy-1H-indole-3-carboxylate

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Methyl 5-methoxy-1H-indole-3-carboxylate Basic information
Product Name:Methyl 5-methoxy-1H-indole-3-carboxylate
Synonyms:METHYL 5-METHOXY-1H-INDOLE-3-CARBOXYLATE;5-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER;RARECHEM AL BF 0096;1H-Indole-3-carboxylic acid, 5-methoxy-, methyl ester;methyl 5-methoxy-1H-indole-3-carboxylic acid;Methyl 5-Methoxy-indole-3-carboxylate;5-Methoxyl-1H-3-Indole-carboxylicacid,, Methyl ester
CAS:172595-68-5
MF:C11H11NO3
MW:205.21
EINECS:
Product Categories:pharmacetical
Mol File:172595-68-5.mol
Methyl 5-methoxy-1H-indole-3-carboxylate Structure
Methyl 5-methoxy-1H-indole-3-carboxylate Chemical Properties
storage temp. Sealed in dry,Room Temperature
AppearanceOff-white to light yellow Solid
Safety Information
MSDS Information
Methyl 5-methoxy-1H-indole-3-carboxylate Usage And Synthesis
UsesMethyl 5-methoxy-1H-indole-3-carboxylate is a useful reactant for the synthesis of tetrahydropyridoindoles via ruthenium-catalyzed decarboxylative C-H alkenylation .
Synthesis
METHYL 3,3-DIMETHOXYPROPIONATE

7424-91-1

4-Methoxyphenylhydrazine hydrochloride

19501-58-7

Methyl 5-methoxy-1H-indole-3-carboxylate

172595-68-5

The general procedure for the synthesis of methyl 5-methoxy-1H-indole-3-carboxylate from methyl 3,3-dimethoxypropionate and 4-methoxyphenylhydrazine hydrochloride was as follows (Intermediate Example 38): 4-methoxyphenylhydrazine hydrochloride (200 mg) and methyl 3,3-dimethoxypropionate (194 mg) were added to acetic acid (8.0 mL). The reaction mixture was stirred at 70 °C for 4.5 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure and the residue was purified by column chromatography (eluent: ethyl acetate/hexane, 1:5→1:3) to afford the target product methyl 5-methoxy-1H-indole-3-carboxylate (259 mg, yield: 97%). The product was characterized by 1H NMR (DMSO-d6): δ 3.8 (3H, s), 3.9 (3H, s), 6.8 (1H, dd), 7.4 (1H, d), 7.5 (1H, d), 8.0 (1H, s), 11.8 (1H, brs).ESI/MS (m/z): 204 ([M-H]-).

References[1] Patent: EP1595866, 2005, A1. Location in patent: Page/Page column 18
Methyl 5-methoxy-1H-indole-3-carboxylate Preparation Products And Raw materials
Raw materialsMethyl 3,3-dimethoxypropionate-->4-Methoxyphenylhydrazine hydrochloride
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