Potassium Carbonate → HCID 71294070, compound

HRID 1747523Notes

Reaction equation

HRID 1747523 reaction equation
C([O:4][CH:5]([C:10]1[CH:11]=[N:12][CH:13]=[C:14](Br)[CH:15]=1)[C:6]([F:9])([F:8])[F:7])(=O)C.[CH3:17][S:18]([O-:20])=[O:19].[Na+].N1CCC[C@H]1C(O)=O.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu](I)I.O>[F:7][C:6]([F:9])([F:8])[CH:5]([C:10]1[CH:11]=[N:12][CH:13]=[C:14]([S:18]([CH3:17])(=[O:20])=[O:19])[CH:15]=1)[OH:4]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 516892Sodium BicarbonateHCID 2733271Sodium methanesulfinateHCID 71293873HCID 71293873, compound

Product 1

HCID 71294070HCID 71294070, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

In DMSO (3.0 mL) was dissolved 1-(5-bromopyridin-3-yl)-2,2,2-trifluoroethyl acetate (429 mg, 1.44 mmol) obtained in Step 3. To the solution were added sodium methanesulfinate (176 mg, 1.73 mmol), copper iodide (I) (41.1 mg, 0.216 mmol), L-proline (49.7 mg, 0.432 mmol) and sodium bicarbonate (36.3 mg, 0.432 mg) and the mixture was stirred at 95° C. for 72 hours. Water was added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure and the residue was dissolved in methanol (10.0 mL). Potassium carbonate (597 mg, 4.32 mmol) was added and the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and water was added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7) to give 2,2,2-trifluoro-1-(5-(methylsulfonyl)pyridin-3-yl)ethanol (61.4 mg, 17% yield).

Workup

  1. extractionExtraction with ethyl acetate
  2. washwashing with saturated brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent in the filtrate was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in methanol (10.0 mL)
  7. stirringthe mixture was stirred at room temperature for 1 hour
  8. customThe solvent was evaporated under reduced pressure and water
  9. additionwas added
  10. extractionExtraction with ethyl acetate
  11. washwashing with saturated brine
  12. dry with materialdrying over anhydrous sodium sulfate
  13. filtrationAfter filtration
  14. customthe solvent in the filtrate was evaporated under reduced pressure
  15. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/7)

Sources & evidence

ORD record
ord-b62d233adb304f30b5a36ca35fcd7b87
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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