[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1F)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.[S-:19][CH2:20][CH3:21].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[S:19][CH2:20][CH3:21])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1A 25 ml round-bottom flask with a magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-9H-β-carboline (102 mg, 0.38 mmol) in 5 ml of anhydrous DMF. To the resulting orange mixture at RT was slowly added sodium thioethoxide (80% pure, 69.7 mg, 0.66 mmol) in powder form. The reaction mixture was stirred at RT for 45 minutes, then added drop-wise to a 5:1 mixture of H2O/saturated sodium bicarbonate (˜30 ml). The resulting precipitated solid was collected by suction filtration, washed with 1:1 hexanes/diethyl ether (2×20 ml), and air-dried to afford 95.0 mg of 6-chloro-7-ethylsulfanyl-8-nitro-9H-β-carboline as an orange solid (79%).
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