Cesium carbonate → HCID 67509189, compound

HRID 623445Notes

Reaction equation

HRID 623445 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[C:4]([CH3:11])[N:3]=1.FC(F)(F)S(O[CH2:18][C:19]([F:22])([F:21])[F:20])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH3:11][C:4]1[CH:5]=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=[C:2]([O:1][CH2:18][C:19]([F:22])([F:21])[F:20])[N:3]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516892Sodium BicarbonateHCID 178466746HCID 178466746, compound

Product 1

HCID 67509189HCID 67509189, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(2-hydroxy-6-methylpyridin-4-yl)ethanone (82 mg, 0.542 mmol, Step-2), 2,2,2-trifluoroethyl trifluoromethanesulfonate (86 microL, 0.60 mmol) and cesium carbonate (350 mg, 1.09 mmol) in DMF (5 mL) is stirred at room temperature for 1.5 hours. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate (10 mL) and extracted with ethyl acetate (30 mL). The organic layer is washed with saturated aqueous sodium hydrogen carbonate (10 mL×2) and dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1) to give 44 mg (35% yield) of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate (30 mL)
  2. washThe organic layer is washed with saturated aqueous sodium hydrogen carbonate (10 mL×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-9d82d6fd2c2b484a8326cb27d284079d
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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