Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | methyl 1H-indole-5-carboxylate | HCID 2737635 | — |
| Product | HCID 58803197 | HCID 58803197 | — |
Reaction Steps
To a solution of methyl 1H-indole-5-carboxylate (1.5 g) in DMF (30 mL) was added NaH (410 mg) at 0° C. The reaction mixture was warmed to 25° C., followed by stirring for 0.5 hours. Then, the reaction mixture was cooled to 0° C. again, and then methyliodide (1.38 mL) was added thereto. The reaction mixture was warmed to 25° C., followed by stirring for 3 hours. To the reaction liquid was added water (50 mL), followed by extraction with EtOAc (50 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, CHCl3:MeOH=100:0 to 98:2) to obtain methyl 1-ethyl-1H-indole-5-carboxylate (1465 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08193378B2 |
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| Source dataset | uspto-grants-2012_06 |
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| ORD ID | ord-ee353fad36ee447e92b1356a56e9979b |
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| Source note | uspto-grants-2012_06 |
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