Methyl iodide → 6-Fluoro-1-methyl-1h-indole

HRID 1372758Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:13]I.[Cl-].[NH4+]>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH3:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In DMF (65 ml) was dissolved 6-fluoroindole (6.10 g, 45.1 mmol). Under stirring at 0° C., sodium hydride (60% in oil, 1.45 g, 36.3 mmol) was added in portions. After stirring at 0° C. for 30 minutes, methyl iodide (2.46 ml, 39.6 mmol) was added to the reaction mixture. The reaction mixture was stirred further at the same temperature for 2.5 hours. A saturated aqueous solution of ammonium chloride was added, followed by extraction with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (5:1, v/v) eluate fractions, 6-fluoro-1-methylindole (6.71 g, 99%) was obtained as a yellow oil.

Workup

stirringAfter stirring at 0° C. for 30 minutes
stirringThe reaction mixture was stirred further at the same temperature for 2.5 hours
extractionfollowed by extraction with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
distillationdistilled under reduced pressure
customto remove the solvent
customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (5:1

Sources & evidence

ORD record: ord-df92aa080d35433b838c7823764eaa50
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157487B2

Reaction notes

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