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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 409902Generated: October 29, 2026

Methyl iodide → Methyl 3-(4-fluorophenyl)-1-methyl-1H-indole-6-carboxylate

https://huagongshe.com/reaction/409902

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
Reactantmethyl 3-(4-fluorophenyl)-1H-indole-6-carboxylateHCID 59625721—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductMethyl 3-(4-fluorophenyl)-1-methyl-1H-indole-6-carboxylateHCID 59625676119.9%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a solution of compound 11d (300 mg, 0.78 mmol) in DMF (3 mL) was added NaH (60% in mineral oil, 68.9 mg, 1.72 mmol) at 0° C. The mixture was stirred at 0° C. for 30 min, then CH3I (0.053 mL, 0.86 mmol) was added and stirring continued at 0° C. for another 1 h. The resulting mixture was diluted with EtOAc and water. The organic layer was washed with brine and concentrated. The residue was recrystallized from heptane, filtered and the solid dried to give compound 12a (265 mg) as a light yellow solid. MS m/z (M+H+) 284.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08759533B2
Source datasetuspto-grants-2014_06
ORD IDord-dfd41a974216407c815b3eaec8ec49d6
Source noteuspto-grants-2014_06