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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 217434Generated: October 29, 2026

Water → HCID 58803197, compound

https://huagongshe.com/reaction/217434

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDimethylformamideHCID 6228—
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactantmethyl 1H-indole-5-carboxylateHCID 2737635—
ProductHCID 58803197HCID 58803197—

Reaction Conditions

Temperature25 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08193378B2
Source datasetuspto-grants-2012_06
ORD IDord-ee353fad36ee447e92b1356a56e9979b
Source noteuspto-grants-2012_06