p-Toluenesulfonic acid → ethyl 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-2-propanoate

HRID 1585074Notes

Reaction equation

HRID 1585074 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=O)[CH2:12][CH2:13][C:14](=O)[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:24][C:25]1[CH:31]=[CH:30][C:28]([N:29]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)=[CH:12][CH:13]=[C:14]2[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 97314-FluoroanilineHCID 10807067Ethyl 4-(methylsulfonyl)-gamma,zeta-dioxobenzeneheptanoate

Product 1

HCID 10525919ethyl 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-2-propanoateYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 4-(methylsulfonyl)-γ,ζ-dioxobenzeneheptanoate (Step 3), (270 mg, 0.79 mmol), 4-fluoroaniline (83 μl, 0.87 mmol) and p-toluenesulfonic acid (25 mg) in toluene (40 ml) was heated at reflux for 24 hours. The reaction mixture was cooled, filtered and concentrated. The crude solid (360 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1) to give ethyl 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-1H-pyrrole-2-propanoate (246 mg, 75%) as a white solid: mp (DSC) 134° C. Anal Calc'd. for C22H22NSFO4 : C, 63.60; H, 5.34; N, 3.37; S, 7.72. Found: C, 63.29; H, 5.51; N, 3.38; S, 8.05.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude solid (360 mg) was purified by chromatography (silica gel, hexane/ethyl acetate, 1/1)

Sources & evidence

ORD record
ord-3d088394131342999acc8314245470a8
Source dataset
uspto-grants-1999_08
Patent number
US05935990

Reaction notes

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