Dimethylformamide → 1-(4-Fluorophenyl)-4-formyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

HRID 1585078Notes

Reaction equation

HRID 1585078 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[CH3:23])=[CH:4][CH:3]=1.CN(C)[CH:26]=[O:27].P(Cl)(Cl)(Cl)=O.C([O-])(=O)C.[Na+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([CH:26]=[O:27])=[C:9]2[CH3:23])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 27657241-(4-Fluorophenyl)-2-methyl-5-(4-methylsulfonylphenyl)pyrrole

Product 1

HCID 108321701-(4-Fluorophenyl)-4-formyl-5-methyl-2-(4-methylsulfonylphenyl)pyrroleYield 71.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole (Example 1) (1.55 g, 4.71 mmol) in dimethylformamide (3.65 ml, 47 mmol) and toluene (20 ml), phosphorous oxychloride (3.5 ml, 37.7 mmol) was added. After stirring for 20 minutes, the reaction mixture was heated at 70° C. for 5 hours. The reaction mixture was cooled, poured into aqueous sodium acetate solution and extracted with ethyl acetate. The organic fractions were washed with 10% aqueous potassium carbonate and water. After drying (Na2SO4), filtration and concentration, the crude yellowish liquid (2.06 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxaldehyde (1.2 g, 71%): mp (DSC) 155° C. Anal Calc'd. for C19H16NSFO3 : C, 63.85; H, 4.51; N, 3.92. Found: C, 63.50; H, 4.66; N, 3.85.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic fractions were washed with 10% aqueous potassium carbonate and water
  4. customAfter drying
  5. filtration(Na2SO4), filtration and concentration
  6. customthe crude yellowish liquid (2.06 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-0d7328f67ce947fc94af5672e0eda7a6
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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