4-methylsulfanyl-1H-indole

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). the reaction mixture stirred at −20° C. for 1 h the crude product extracted into benzene (˜250 mL) The organic layer was washed with brine dried over Na2SO4 the mixture stirred at RT for 1 h The solvent was removed under vacuum the insoluble solid filtered off The solvent was removed by evaporation to dryness The product was purified by column chromatography (0 to 25% EtOAc/hexane)