Cesium carbonate → HCID 18551224, compound

HRID 1698834Notes

Reaction equation

HRID 1698834 reaction equation
[Br:1][C:2]1[C:11]([NH:12][C:13](=[O:26])[C:14](=[O:25])[CH2:15][C:16]([CH3:24])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH3:17])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][O:5][C:6]2=[O:7].[F:27][C:28]([Si](C)(C)C)([F:30])[F:29].C(=O)([O-])[O-].[Cs+].[Cs+].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O.O1CCCC1.O>[Br:1][C:2]1[C:11]([NH:12][C:13](=[O:26])[C:14]([OH:25])([C:28]([F:30])([F:29])[F:27])[CH2:15][C:16]([CH3:17])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH3:24])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][O:5][C:6]2=[O:7]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 185512024-Bromo-5-(4-methyl-2-oxo-4-phenyl-valeroylamino)-phthalide

Product 1

HCID 18551224HCID 18551224, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

350 mg of 4-bromo-5-(4-methyl-2-oxo-4-phenyl-valeroyl-amino)-phthalide is dissolved under argon in 15 ml of dimethylformamide and mixed with 0.77 ml of trifluoromethyl-trimethylsilane and 350 mg of cesium carbonate while being cooled with ice. After 3 hours of stirring at room tempera-ture, 5 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran and some drops of water are added and stirred for one hour at room temperature. After 100 ml of water is added, it is extracted with ethyl acetate, the organicphase is dried (Na2SO4) and concentrated by evaporation. 250 mg of 4-bromo-5-(2-hydroxy-4-methyl-4-phenyl-2-trifluoromethyl-valeroylamino)-phthalide, melting point 187-194° C., is obtained.

Workup

  1. temperaturewhile being cooled with ice
  2. extractionit is extracted with ethyl acetate
  3. dry with materialthe organicphase is dried (Na2SO4)
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-11579327e2cf445b96d8ce9d6e1a6b54
Source dataset
uspto-grants-2002_02
Patent number
US06344454B1

Reaction notes

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