Benzene → HCID 18688800, compound

HRID 128859Notes

Reaction equation

HRID 128859 reaction equation
[C:1]1([CH3:28])[CH:6]=[CH:5][C:4]([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(C(O)=O)[CH2:11]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[F:53][C:54]1[CH:60]=[C:59]([F:61])[CH:58]=[CH:57][C:55]=1[NH2:56].[CH:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1>O>[F:53][C:54]1[CH:60]=[C:59]([F:61])[CH:58]=[CH:57][C:55]=1[NH:56][C:51]([NH:48][CH:11]1[C:12]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]1[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:28])=[CH:2][CH:3]=1)(=[O:8])=[O:9])=[O:36]

Participants

7

Reactant 5

HCID 241BenzeneHCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 18688868HCID 18688868, compound

Product 1

HCID 18688800HCID 18688800, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred mixture of 1.05 g of 1-(p-toluenesulfonyl)-3-phenylindole-3-carboxylic acid and 0.60 cc of diphenylphosphoryl azide in 10 cc of benzene was added dropwise 0.39 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 15 minutes and then heated under reflux for 30 minutes. After cooling, 0.285 cc of 2,4-difluoroaniline was added and then stirred at room temperature for 30 minutes, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and extracted with ethyl acetate. The extract was dried over magnesium sulfate, and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/3) to obtain 780 mg of compound 120. Yield 55.8%, m.p. 244°-246° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 30 minutes
  3. temperatureAfter cooling
  4. stirringstirred at room temperature for 30 minutes
  5. temperatureby refluxing for 2 hours
  6. temperatureAfter cooling
  7. extractionextracted with ethyl acetate
  8. dry with materialThe extract was dried over magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent
  11. customThe crude product thus obtained
  12. customwas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/3)

Sources & evidence

ORD record
ord-79fe91e70b97438e98aab6a9e21c202d
Source dataset
uspto-grants-1995_11
Patent number
US05464863

Reaction notes

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