Methyl iodide → 5-fluoro-1-methyl-1H-indole-3-carbaldehyde

Temperature

0 °C

In DMF (100 ml) was dissolved 5-fluoroindol-3-carbaldehyde (5.17 g, 36.7 mmol). To the resulting solution was added sodium hydride (60% in oil, 1.39 g, 34.9 mmol) in portions under stirring at 0° C. After the reaction mixture was stirred at the same temperature for 1 hour, methyl iodide (4.57 ml, 73.4 mmol) was added thereto at 0° C. The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was poured in 1N HCl, followed by extraction with ether. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was crystallized by adding thereto chloroform/hexane. The crystals thus precipitated were collected by filtration under reduced pressure and dried under reduced pressure to give 5-fluoro-1-methylindole-3-carbaldehyde (2.53 g, 39%) as a white crystalline powder.

1. stirringAfter the reaction mixture was stirred at the same temperature for 1 hour
2. customat 0° C
3. stirringThe resulting mixture was stirred at room temperature for 18 hours
4. extractionfollowed by extraction with ether
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. distillationdistilled under reduced pressure
8. customto remove the solvent
9. customThe residue was crystallized
10. additionby adding
11. customThe crystals thus precipitated
12. filtrationwere collected by filtration under reduced pressure
13. customdried under reduced pressure

ORD record

ord-8ef8b9b6617a4f3aa1c076c07b81cca7

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07157487B2