p-Toluenesulfonic acid → 1-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

HRID 1585067Notes

Reaction equation

HRID 1585067 reaction equation
CC1(C)CO[CH:5]([CH2:8][CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)=O)OC1.[F:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:23][C:24]1[CH:30]=[CH:29][C:27]([N:28]2[CH:5]=[CH:8][CH:9]=[C:10]2[C:12]2[CH:13]=[CH:14][C:15]([S:18]([CH3:21])(=[O:19])=[O:20])=[CH:16][CH:17]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 97314-FluoroanilineHCID 10496371HCID 10496371, compound

Product 1

HCID 108291321-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)pyrroleYield 45%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-(5,5-dimethyl-1,3-dioxan-2-yl)-1-[4-(methylsulfonyl)phenyl]propan-1-one (Step 5), (1.6 g, 4.9 mmol), 4-fluoroaniline (510 μl, 5.4 mmol) and p-toluenesulfonic acid (120 mg) in toluene (200 ml) was heated to reflux for 72 hours. The reaction mixture was cooled, filtered and concentrated. The crude solid (2.48 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4) to give 1-[4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]-1H-pyrrole (695 mg, 45%) as a white solid: mp (DSC) 163° C. Anal Calc'd. for C17H14NSFO2 : C, 64.75; H, 4.47; N, 4.44. Found: C, 64.71; H, 4.53; N, 4.43.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 72 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude solid (2.48 g) was purified by chromatography (silica gel, hexane/ethyl acetate, 6/4)

Sources & evidence

ORD record
ord-74d7b7a5950245daa18f1e5979fffa39
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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