Benzenesulfonyl chloride → Ethyl 5-(4-fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylate

HRID 554269Notes

Reaction equation

HRID 554269 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]([CH3:13])=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:21]1([S:27](Cl)(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([S:27]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:29])=[O:28])[C:11]([CH3:13])=[C:10]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 27211259Ethyl 5-(4-fluorophenyl)-2-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 66924952Ethyl 5-(4-fluorophenyl)-2-methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carboxylateYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(4-fluorophenyl)-2-methyl-1H-pyrrole-3-carboxylate (4.95 g) was dissolved in absolute tetrahydrofuran (50 mL), and sodium hydride (60% in oil, 1.20 g) was added under ice-cooling. The mixture was stirred at room temperature for 15 min, and benzenesulfonyl chloride (5.30 g) was added dropwise. The reaction mixture was stirred at room temperature for 18 hr, ice water was added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:2) to give the title compound as a solid (yield 2.75 g, 35%).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 18 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:2)

Sources & evidence

ORD record
ord-ddddb7db318446c789b3b1ce864cb521
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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