| Identification | Back Directory | [Name]
Methyl 5-methoxy-1H-indole-3-carboxylate | [CAS]
172595-68-5 | [Synonyms]
RARECHEM AL BF 0096
Methyl 5-Methoxy-indole-3-carboxylate
METHYL 5-METHOXY-1H-INDOLE-3-CARBOXYLATE
methyl 5-methoxy-1H-indole-3-carboxylic acid
5-METHOXY-1H-INDOLE-3-CARBOXYLIC ACID METHYL ESTER
5-Methoxyl-1H-3-Indole-carboxylicacid,, Methyl ester
1H-Indole-3-carboxylic acid, 5-methoxy-, methyl ester | [Molecular Formula]
C11H11NO3 | [MDL Number]
MFCD06203662 | [MOL File]
172595-68-5.mol | [Molecular Weight]
205.21 |
| Hazard Information | Back Directory | [Uses]
Methyl 5-methoxy-1H-indole-3-carboxylate is a useful reactant for the synthesis of tetrahydropyridoindoles via ruthenium-catalyzed decarboxylative C-H alkenylation . | [Synthesis]
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 |
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