[CH3:1][S:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].[CH3:14]I>CN(C=O)C>[CH3:14][N:9]1[C:10]2[C:6](=[CH:5][CH:4]=[C:3]([S:2][CH3:1])[CH:11]=2)[CH:7]=[CH:8]1A solution of 6-methylsulfanyl-1H-indole (6.8 g, 42 mmol) in DMF (50 mL) was added to a slurry of NaH (55 mmol) in DMF(10 mL) at 0° C. over a period of 10 minutes. After stirring for 1 hour at 0° C., CH3I (4.0 ml,64 mmol) was added and the mixture stirred for 30 minutes at 0° C., then at room temperature for 1 hour, then poured into ice/H2O and extracted with EtOAc. The organic phase was washed with saturated NaCl solution, dried over MgSO4, filtered and evaporated to give 6.7 g (91.0%) of 1-methyl-6-methylsulfanyl-1H-indole as a yellow oil after flash column chromatography.
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