Methyl iodide → HCID 14668766, compound

NaH (637 mg, 15.87 mmol, 60% dispersion) was added in portions to a solution of 1,5,6,7-tetrahydro-indole-4-thione (2 g, 13.23 mmol) in THF (100 mL) at −20° C. under N2 and stirred for 20 min. MeI (1.3 mL, 19.84 mmol) was added in dry THF (10 mL), and the reaction mixture stirred at −20° C. for 1 h. The reaction mixture was then poured into NaHCO3 (sat'd aq), and the crude product extracted into benzene (˜250 mL). The organic layer was washed with brine, and dried over Na2SO4. To this was added DDQ (3 g, 13.23 mmol), and the mixture stirred at RT for 1 h. The solvent was removed under vacuum, the residue taken up in CHCl3, and the insoluble solid filtered off. The solvent was removed by evaporation to dryness and the solid immobilized on silica gel. The product was purified by column chromatography (0 to 25% EtOAc/hexane) to provide 4-methylsulfanyl-1H-indole (1.2568 g, 58.2% yield).

1. stirringthe reaction mixture stirred at −20° C. for 1 h
2. extractionthe crude product extracted into benzene (˜250 mL)
3. washThe organic layer was washed with brine
4. dry with materialdried over Na2SO4
5. stirringthe mixture stirred at RT for 1 h
6. customThe solvent was removed under vacuum
7. filtrationthe insoluble solid filtered off
8. customThe solvent was removed by evaporation to dryness
9. customThe product was purified by column chromatography (0 to 25% EtOAc/hexane)

ORD record

ord-86a2d3715b7a468c92b346ee87a9833f

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399462B2