Pyridine → HCID 23158307, compound

HRID 601653Notes

Reaction equation

HRID 601653 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])[CH:28]=[C:29]([CH3:33])[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])[CH:28]=[C:29]([CH3:33])[O:30]2)=[CH:25][CH:24]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 53553097-hydroxy-2-methyl-4H-1-benzopyran-4-one

Product 1

HCID 23158307HCID 23158307, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 0.2 ml of trifluoromethansulfonic anhydride was added at 0° C. to 3 ml solution of pyridine with 10 mg of 7-hydroxy-2-methyl-4H-chromen-4-one, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, extracted with ethyl acetate. Ethyl acetate layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by silicagel chromatography (hexane/ethyl acetate=10/1) to obtain 112 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. distillationThe solvents were distilled outunder reduced pressure
  5. customthe residues were separated
  6. custompurified by silicagel chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-dbc39647c4f44499920a8e40a616d81d
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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