Dimethyl Disulfide → 1h-Indole,2-methyl-5-(methylthio)-1-(phenylsulfonyl)-
Reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15](Br)=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH3:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[CH3:26][S:27]SC>C1COCC1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:27][CH3:26])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH3:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Procedure
To a chilled solution of 1-benzenesulfonyl-5-bromo-2-methyl-1H-indole (350 mg, 0.99 mmol) in 4 mL of THF was added 440 μL (1.10 mmol) of n-BuLi (2.5 M solution in hexanes), followed by dimethyl disulfide (100 μL, 1.11 mmol). The mixture was stirred as it warmed to room temperature and was then quenched with ammonium chloride and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with three 15 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was adsorbed onto silica gel and chromatographed on silica gel using ethyl acetate-hexanes (1:99, then 2:98) to afford 156 mg (44.3% yield) of 1-benzenesulfonyl-2-methyl-5-methylsulfanyl-1H-indole as a clear oil.
Workup
- customwas then quenched with ammonium chloride
- extractionextracted with three 15 mL portions of ethyl acetate
- washThe combined organic layers were washed with three 15 mL portions of brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customchromatographed on silica gel
Sources & evidence
- ORD record
- ord-bf90f3c01fa946029593877ae4af8cd6
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741897B2
Reaction notes
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