Cesium carbonate → HCID 90418667, compound

HRID 633604Notes

Reaction equation

HRID 633604 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[OH:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:1][C:2]1[C:3]([O:20][C:14]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=2[F:12])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 2308893-Bromo-2-chloro-5-nitropyridine

Product 1

HCID 90418667HCID 90418667, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 3-bromo-2-chloro-5-nitropyridine (0.237 g, 1 mmol), 2,4-difluorophenol (0.13 g, 1 mmol) and cesium carbonate (0.326 g, 1 mmol) in dimethyl sulfoxide (2 mL) was reacted in a Biotage microwave reactor at 80° C. for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography (silica gel, 0-20% ethyl acetate in heptanes) to provide 0.312 g (94%) of the title compound.

Workup

  1. customwas reacted in a Biotage microwave reactor at 80° C. for 30 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (silica gel, 0-20% ethyl acetate in heptanes)

Sources & evidence

ORD record
ord-8584009cc15447ea8c6af0333a6916df
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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