Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-5-(2-pyridinyl)-1H-pyrrole-3-carboxaldehyde

HRID 554332Notes

Reaction equation

HRID 554332 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][CH:10]=[C:9]([CH:12]=[O:13])[CH:8]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.[Cl-].[Na+].O>[C:31]1([S:37]([N:11]2[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][C:9]([CH:12]=[O:13])=[CH:10]2)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 86232757HCID 86232757, compound

Product 1

HCID 862327121-(Phenylsulfonyl)-5-(2-pyridinyl)-1H-pyrrole-3-carboxaldehydeYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (16 mL) of 5-(pyridin-2-yl)-1H-pyrrole-3-carbaldehyde (80 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 56 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (307 mg) was added dropwise and the mixture was stirred for 30 min. Benzenesulfonyl chloride (165 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1), and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 85 mg, 59%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was further stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1→1:1)
  8. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-46e7e053d4764526966e1508cfa51008
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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