Methyl iodide → 5-Chloro-1-methylindole

Temperature

0 °C

In DMF (65 ml) was dissolved 5-chloroindole (5.00 g, 33.0 mmol), followed by the addition of sodium hydride (60% in oil, 1.45 g, 36.3 mmol) in portions under stirring at 0° C. After the reaction mixture was stirred further for 30 minutes at the same temperature, methyl iodide (2.46 ml, 39.6 mmol) was added. The resulting mixture was stirred at 0° C. for 30 minutes. Ice water was added to the reaction mixture, 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 (3:1, v/v) eluate fractions, 5-chloro-1-methylindole (5.89 g, 100%) was obtained as a yellow oil.

1. additionwas added
2. stirringThe resulting mixture was stirred at 0° C. for 30 minutes
3. extractionfollowed by extraction with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous sodium sulfate
6. distillationdistilled under reduced pressure
7. customto remove the solvent
8. customThe residue was purified by chromatography on a silica gel column, whereby from n-hexane-ethyl acetate (3:1

ORD record

ord-769c1b1a89b2456a8d89a02165c0282f

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2