Methyl iodide → 4-Fluoro-1-methyl-1H-indole

Temperature

0 °C

In DMF (40 ml) was dissolved 4-fluoroindole (2.00 g, 14.8 mmol). To the resulting solution was added sodium hydride (60% in oil, 0.71 g, 17.8 mmol) in portions under stirring at 0° C. After the reaction mixture was stirred for 40 minutes at the same temperature, methyl iodide (1.11 ml, 17.8 mmol) was added at 0° C. The reaction mixture was stirred further at the same temperature for 4 hours. A saturated aqueous solution of ammonium chloride was added to terminate the reaction. The reaction mixture was extracted with ether, and 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, 4-fluoro-1-methylindole (2.20 g, 100%) was obtained as a yellow oil.

1. additionwas added at 0° C
2. stirringThe reaction mixture was stirred further at the same temperature for 4 hours
3. customto terminate
4. customthe reaction
5. extractionThe reaction mixture was extracted with ether
6. washthe extract was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. distillationdistilled under reduced pressure
9. customto remove the solvent
10. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (5:1

ORD record

ord-677d36369c814499be04f259af5b3aab

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2