Cesium carbonate → HCID 67329823, compound

HRID 1675297Notes

Reaction equation

HRID 1675297 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:34])[CH2:15][C@@H:16]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH:30](Br)[CH2:31][CH3:32])=[CH:24][CH:23]=1)[C:17]1[CH:21]=[CH:20][O:19][N:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:41][C:42]([F:51])([F:50])[C:43]1[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=1>CN(C=O)C.O>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:34])[CH2:15][C@H:16]([C:17]1[CH:21]=[CH:20][O:19][N:18]=1)[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH:30]([O:49][C:46]2[CH:47]=[CH:48][C:43]([C:42]([F:41])([F:50])[F:51])=[CH:44][CH:45]=2)[CH2:31][CH3:32])=[CH:24][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 678744-(Trifluoromethyl)phenolHCID 67330915HCID 67330915, compound

Product 1

HCID 67329823HCID 67329823, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The bromide 49.1 (90 mg, 0.17 mmol) was dissolved in DMF (2.0 mL). Cesium carbonate (220 mg, 0.68 mmol) and 4-trifluoromethylphenol (110 mg, 0.68 mmol) were added to the solution and the mixture was then heated with stirring for three hours. The reaction mixture was then cooled to room temperature and diluted with water. The mixture was extracted with EtOAc (2×50 mL). The combined organic layers were washed with 1M lithium chloride solution (1×25 mL), water (1×25 mL) and brine (1×25 mL), and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue purified by medium pressure chromatography (silica, 0 to 60% EtOAc: hexanes) to obtain 49.2 (23 mg). MS ESI (pos.): m/e 609.1 (M+H).

Workup

  1. temperaturethe mixture was then heated
  2. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with 1M lithium chloride solution (1×25 mL), water (1×25 mL) and brine (1×25 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue purified by medium pressure chromatography (silica, 0 to 60% EtOAc: hexanes)

Sources & evidence

ORD record
ord-55aaab09ace64db19a9dee2b4bff643e
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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