Sodium Sulfate → {1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol

HRID 2264626Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:20](OCC)=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].C1(C)C=CC=CC=1.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.C(OCC)(=O)C.CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[C:12]2[CH2:20][OH:21])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 1.4 g of ethyl 1-[(4-bromophenyl)sulfonyl]-1H-indole-2-carboxylate in 10 mL of THF, 7.6 mL of diisobutylalminum hydride-toluene solution was added at a temperature of −60° C. or lower, and the resulting mixture was stirred under cooling in a dry ice-acetone bath for 5 hours and under ice cooling for 2 hours. After the solution was cooled to −70° C., 5 g of sodium sulfate decahydrate and 5 mL of methanol were added, the resulting mixture was warmed to room temperature, 50 mL of ethyl acetate and anhydrous sodium sulfate were added, insoluble matter was removed by filtration, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to obtain 0.97 g of {1-[(4-bromophenyl)sulfonyl]-1H-indol-2-yl}methanol as a pale violet solid. EI: 365, 367

Workup

temperatureunder cooling in a dry ice-acetone bath for 5 hours and under ice cooling for 2 hours
temperaturethe resulting mixture was warmed to room temperature
custominsoluble matter was removed by filtration
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record: ord-15f54747040349eea6a878198eab5a52
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855225B2

Reaction notes

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