Hydrochloric Acid → 5-fluoro-3-iodo-1-methyl-1H-pyridin-2-one

HRID 509936Notes

Reaction equation

HRID 509936 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([I:9])[C:5]([OH:8])=[N:6][CH:7]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].IC.Cl>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([I:9])[C:5](=[O:8])[N:6]([CH3:10])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178517765HCID 178517765, compound

Product 1

HCID 672008475-fluoro-3-iodo-1-methyl-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 5-fluoro-3-iodo-pyridin-2-ol (31, 200 g, 838 mmol) in 3000 mL of acetone was cooled in an ice water bath. Cesium carbonate (354 g, 1088 mmol) was added, then iodomethane (58.1 mL, 929 mmol) was added dropwise over 30 minutes. The reaction was stirred overnight at room temperature. The reaction was concentrated under vacuum and the resulting material partitioned between ethyl acetate and water. The aqueous layer was isolated and adjusted to pH 3-4 with 3 N hydrochloric acid, then extracted with ethyl acetate. The combined organic layers were concentrated under vacuum to provide the desired compound as an off white solid. (32, 150 g, 593 mmol, 70.8%).

Workup

  1. concentrationThe reaction was concentrated under vacuum
  2. customthe resulting material partitioned between ethyl acetate and water
  3. customThe aqueous layer was isolated
  4. extractionextracted with ethyl acetate
  5. concentrationThe combined organic layers were concentrated under vacuum

Sources & evidence

ORD record
ord-d9bc881b37db43b5a3981f4b2964adca
Source dataset
uspto-grants-2015_08
Patent number
US09096593B2

Reaction notes

Loading…