Benzenesulfonyl chloride → 1-benzenesulfonyl-4-trifluoromethyl-1H-indole
Reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1>[C:16]1([S:22]([N:9]2[C:10]3[C:6](=[C:5]([C:4]([F:3])([F:14])[F:15])[CH:13]=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1Participants
Procedure
370 mg of NaH at 60% in oil are added to a solution of 0.85 g of 4-trifluoromethyl-1H-indole in 15 ml of tetrahydrofuran, under an inert atmosphere. The reaction mixture is stirred at ambient temperature for one hour and then 0.88 ml of benzenesulfonyl chloride is added dropwise and the stirring is continued for 16 hours. The reaction mixture is then poured into a 10% ammonium chloride solution, extracted with ethyl acetate and dried over magnesium sulfate. After filtration and concentration under reduced pressure, the residue is purified by silica column chromatography, elution being carried out with a mixture of heptane and diisopropyl ether (98/2, then 95/5: v/v), so as to give 1.08 g of 1-benzenesulfonyl-4-trifluoromethyl-1H-indole in the form of a pale yellow oil which is used as it is in the next step.
Workup
- waitthe stirring is continued for 16 hours
- extractionextracted with ethyl acetate
- dry with materialdried over magnesium sulfate
- filtrationAfter filtration and concentration under reduced pressure
- customthe residue is purified by silica column chromatography, elution
- additionbeing carried out with a mixture of heptane and diisopropyl ether (98/2
Sources & evidence
- ORD record
- ord-71a62556b4da484a8b14adb4277f6544
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133168B2
Reaction notes
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