Benzenesulfonyl chloride → 6-fluoro-3-iodo-1-(phenylsulfonyl)-1H-indole

HRID 1692889Notes

Reaction equation

[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[Cl-].[NH4+]>[F:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([I:1])=[CH:3][N:4]2[S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 3-iodo-6-fluoroindole (0.50 g, 1.92 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion, 115 mg, 2.87 mmol). The resulting mixture was then stirred at 0° C. for 5 minutes before the addition of benzenesulfonyl chloride (0.37 mL, 2.9 mmol). After stirring at 0° C. for 30 minutes, the reaction was allowed to warm to room temperature and stirred at room temperature for 30 minutes. The reaction mixture was then diluted with saturated ammonium chloride. The aqueous mixture was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (0-50% gradient EtOAc-heptane) to give 6-fluoro-3-iodo-1-(phenylsulfonyl)-1H-indole (0.852 g, quant.).

Workup

temperatureto warm to room temperature
stirringstirred at room temperature for 30 minutes
extractionThe aqueous mixture was extracted three times with EtOAc
washThe combined organic extracts were washed with brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography (0-50% gradient EtOAc-heptane)

Sources & evidence

ORD record: ord-eabc90a1e73344bfbf6242cdad357227
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158625B2

Reaction notes

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