Cesium carbonate → HCID 18551224, compound

HRID 1266446Notes

Reaction equation

HRID 1266446 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 organic phase 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 organic phase is dried (Na2SO4)
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d095dd88622a42c29d9afb9868b1b6c9
Source dataset
uspto-grants-2003_04
Patent number
US06548534B2

Reaction notes

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