N-bromobutanimide → ethyl 3-bromo-6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate

HRID 2299225Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH:13]1[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH2:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].[Br:24]N1C(=O)CCC1=O>ClC1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:24][CH:16]1[CH2:15][CH2:14][CH:13]([S:10](=[O:11])(=[O:12])[NH:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution -of ethyl 6-(N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (100 mg) obtained in Example 3 in chlorobenzene (2 ml), N-bromosuccinimide (56.7 mg) and 2,2′-azobisisobutyronitrile (0.5 mg) were added and the mixture was stirred at 90° C. for 7 hours. The reaction mixture was combined with an ice-water (20 ml), extracted with ethyl acetate (20 ml), washed with saturated brine (20 ml) and dried over anhydrous sodium sulfate. The solvent was distilled off and the resultant residue was purified by flash column chromatography on silica gel (eluent: ethyl acetate/hexane=1/20→ethyl acetate/hexane=1/10) and crystallized from hexane to yield ethyl 3-bromo-6-[N-(2,4-difluorophenyl)sulfamoyl]-1-cyclohexene-1-carboxylate (Compound 85, 27 mg) as colorless powdery crystals.

Workup

extractionextracted with ethyl acetate (20 ml)
washwashed with saturated brine (20 ml)
dry with materialdried over anhydrous sodium sulfate
distillationThe solvent was distilled off
customthe resultant residue was purified by flash column chromatography on silica gel (eluent: ethyl acetate/hexane=1/20→ethyl acetate/hexane=1/10)
customcrystallized from hexane

Sources & evidence

ORD record: ord-0b9482a013ee4821b003211c88dc594d
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06495604B1

Reaction notes

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