Cesium carbonate → HCID 90417101, compound

HRID 633516Notes

Reaction equation

HRID 633516 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:19]2[C:14](=[C:15]([O:20][CH3:21])[N:16]=[CH:17][CH:18]=2)[N:13]([CH3:22])[CH:12]=1.[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[OH:31].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[F:23][C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:25]=1[O:31][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1[C:19]2[C:14](=[C:15]([O:20][CH3:21])[N:16]=[CH:17][CH:18]=2)[N:13]([CH3:22])[CH:12]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 90387914HCID 90387914, compound

Product 1

HCID 90417101HCID 90417101, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of Example 2B (0.123 g, 0.408 mmol), 2,4-difluorophenol (0.069 g, 0.531 mmol) and cesium carbonate (0.173 g, 0.531 mmol) in dimethylsulfoxide (5 mL) was heated at 110° C. for 1 hour. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography (silica gel, 20-50% ethyl acetate in hexanes) to provide 0.16 g (95%) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (silica gel, 20-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-797215df29a44c03be4bf1769755f078
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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