Sodium Hydroxide → HCID 58349828, compound

HRID 1782347Notes

Reaction equation

HRID 1782347 reaction equation
[F:1][C:2]1[C:7]([C:8]2[N:12](S(C3C=CC=CC=3)(=O)=O)[CH:11]=[C:10]([CH:22]=[O:23])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>CO.O1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH:22]=[O:23])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 866239745-(2-fluoropyridin-3-yl)-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 58349828HCID 58349828, compoundYield 79.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-(2-Fluoropyridin-3-yl)-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde (2.25 g) was dissolved in methanol (20 mL) and tetrahydrofuran (20 mL), a 8 mol/L aqueous sodium hydroxide solution (20 mL) was added dropwise at room temperature and the mixture was stirred for 1 hr. The reaction mixture was diluted with saturated brine, 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. Ethyl acetate was added to the residue and insoluble crystals were collected by filtration to give the title compound as pale-brown crystals (yield 1.03 g, 79%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionEthyl acetate was added to the residue and insoluble crystals
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-3ec90486c2354644810e077b509e47b2
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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