4-Fluoroaniline → 1-(4-Fluorophenyl)-4-methoxycarbonyl-5-methyl-2-(4-methylsulfonylphenyl)pyrrole

HRID 1415762Notes

Reaction equation

HRID 1415762 reaction equation
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([C:9](=O)[CH2:10][CH:11]([C:16]([CH3:18])=O)[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1>C(O)(=O)C>[F:22][C:23]1[CH:29]=[CH:28][C:26]([N:27]2[C:16]([CH3:18])=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[C:9]2[C:8]2[CH:20]=[CH:21][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 97314-FluoroanilineHCID 21862871Methyl 2-(4-methylsulfonylphenacyl)acetoacetate

Product 1

HCID 218628141-(4-Fluorophenyl)-4-methoxycarbonyl-5-methyl-2-(4-methylsulfonylphenyl)pyrroleYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.00 g (9.6 mmol) of methyl 2-(4-methylsulfonylphenacyl)acetoacetate [prepared as described in step (ii) above] were dissolved in 100 ml of acetic acid and 0.97 g (8.7 mmol) of 4-fluoroaniline was added to the resulting solution. The resulting mixture was then heated under reflux for 5 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, a saturated aqueous solution of sodium hydrogencarbonate was added to the residue and the mixture was extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The residue was applied to a silica gel chromatography column and eluted with a 1:2 by volume mixture of ethyl acetate and hexane, to give 3.10 g of the title compound as a white powder (yield 92%), melting at 154-155° C.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureunder reflux for 5 hours
  3. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  4. additiona saturated aqueous solution of sodium hydrogencarbonate was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure
  10. washeluted with a 1:2 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c86b43e071df4ef9ab187fbed35b38e0
Source dataset
uspto-grants-1999_06
Patent number
US05908858

Reaction notes

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