Chloroacetone → HCID 66738338, compound

HRID 1640894Notes

Reaction equation

HRID 1640894 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[C:4]([I:9])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:17][C:18](=[O:20])[CH3:19]>CN(C=O)C>[F:1][C:2]1[N:7]=[CH:6][C:5]([O:8][CH2:17][C:18](=[O:20])[CH3:19])=[C:4]([I:9])[CH:3]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 666745926-Fluoro-4-iodopyridin-3-ol

Product 1

HCID 66738338HCID 66738338, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cool a suspension of 6-fluoro-4-iodo-pyridin-3-ol (1.6 g, 6.69 mmol) and K2CO3 (2.8 g, 20.1 mmol) in DMF (10 mL) to 0° C. in an ice bath under nitrogen. Add chloroacetone (0.78 g, 8.03 mmol) during a period of 30 min. Stir the mixture at RT for 1.5 h. Add water and extract with ethyl acetate. Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (hexane to 10% ethyl acetate in hexane) to afford the title compound (1.5 g, 76%). MS (ES) m/z 296 [M+1]+.

Workup

  1. temperatureCool
  2. extractionAdd water and extract with ethyl acetate
  3. washWash the solution with aqueous saturated sodium chloride
  4. dry with materialDry over sodium sulfate
  5. concentrationConcentrate the solution in vacuo
  6. customPurify by column chromatography (hexane to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f21918dbf14242098a66e76cee902935
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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