Pyridine → HCID 23158349, compound

HRID 601647Notes

Reaction equation

HRID 601647 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].N1C=CC=CC=1.O[C:23]1[CH:32]=[C:31]2[C:26]([C:27](=[O:34])[C:28]([CH3:33])=[CH:29][O:30]2)=[CH:25][CH:24]=1>O>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:23]1[CH:32]=[C:31]2[C:26]([C:27](=[O:34])[C:28]([CH3:33])=[CH:29][O:30]2)=[CH:25][CH:24]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 13419593HCID 13419593, compound

Product 1

HCID 23158349HCID 23158349, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 0.23 ml of trifluoromethansulfonic anhydride was added at 0° C. to 3 ml solution of pyridine with 120 mg of 7-hydroxy-3-methyl-4H-chromen-4-one, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, and extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and then dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, residues were separated and purified with silicagel chromatography (hexane/ethyl acetate=10/1) to obtain 183 mg of the above compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washEthyl acetate layer was washed with saturated saline solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. distillationAfter distilling out the solvents under reduced pressure, residues
  5. customwere separated
  6. custompurified with silicagel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-295134fb4db14bab8c9b489399e69da1
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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