Trifluoromethanesulfonic anhydride → Methyl 2-phenyl-6-{[(trifluoromethyl)sulfonyl]oxy}pyridine-4-carboxylate

HRID 1096958Notes

Reaction equation

HRID 1096958 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O=[C:17]1[CH:22]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:20]=[C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:18]1>N1C=CC=CC=1>[C:27]1([C:19]2[CH:20]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[CH:22]=[C:17]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[N:18]=2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydride2×HCID 57931020Methyl 2-oxo-6-phenyl-1,2-dihydropyridine-4-carboxylate

Product 1

HCID 57930938Methyl 2-phenyl-6-{[(trifluoromethyl)sulfonyl]oxy}pyridine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

With cooling with ice, trifluoromethanesulfonic acid anhydride (3.7 mL) was added to a pyridine (80 mL) solution of methyl 2-oxo-6-phenyl-1,2-dihydropyridine-4-carboxylate (2.8 g), and this was stirred for 10 minutes with cooling with ice, and then at room temperature for 2 hours. With further cooling with ice, trifluoromethanesulfonic acid anhydride (1 mL) was added to it, stirred at that temperature for 5 minutes and then overnight at room temperature. The reaction liquid was concentrated under reduced pressure, then ethyl acetate was added thereto, and the formed precipitate was taken away through filtration. Water was added to the filtrate, extracted with ethyl acetate, and the organic layer was washed with water and saturated saline water. This was dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound as a yellow powder.

Workup

  1. temperaturewith cooling with ice
  2. waitat room temperature for 2 hours
  3. additionwas added to it
  4. stirringstirred at that temperature for 5 minutes
  5. customovernight
  6. customat room temperature
  7. customThe reaction liquid
  8. concentrationwas concentrated under reduced pressure
  9. additionethyl acetate was added
  10. filtrationthe formed precipitate was taken away through filtration
  11. additionWater was added to the filtrate
  12. extractionextracted with ethyl acetate
  13. washthe organic layer was washed with water and saturated saline water
  14. dry with materialThis was dried with anhydrous sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated under reduced pressure
  17. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9930feea2c9b46dba4443830d018e4e4
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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