Dichloromethane → 5-[(3-Chloropyridin-4-yl)(2,5-difluorophenyl)methylsulfonyl]-2-fluoropyridine

HRID 748854Notes

Reaction equation

HRID 748854 reaction equation
[F-:1].[K+].Cl[C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH:13]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[Cl:28])[C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])(=[O:12])=[O:11])=[CH:6][N:5]=1.ClCCl.C(OCC)(=O)C>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C>[Cl:28][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:22]=1[CH:13]([C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[F:21])[S:10]([C:7]1[CH:8]=[CH:9][C:4]([F:1])=[N:5][CH:6]=1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 522689Potassium FluorideHCID 231146702-Chloro-5-[(3-chloropyridin-4-yl)(2,5-difluorophenyl)methylsulfonyl]pyridine

Product 1

HCID 597507955-[(3-Chloropyridin-4-yl)(2,5-difluorophenyl)methylsulfonyl]-2-fluoropyridineYield 7%

Reagents, catalysts & solvents 2

HCID 2724163Tetraphenylphosphonium BromideCatalystHCID 6342AcetonitrileSolvent

Procedure

Potassium fluoride (94 mg, 1.60 mmol) and tetraphenylphosphonium bromide (134 mg, 0.32 mmol) were added to a solution of 2-chloro-5-[(3-chloropyridin-4-yl) (2,5-difluorophenyl)methylsulfonyl]pyridine (66 mg, 0.16 mmol) in acetonitrile (2 ml). The resulting mixture was heated under reflux for 16 hours. The reaction mixture was cooled to room temperature. Dichloromethane was added and the mixture was washed with water. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column and a fraction obtained from the elution portion with hexane:ethyl acetate=17:3 was concentrated under reduced pressure, whereby the title compound (4.5 mg, 0.011 mmol, 7%) was obtained as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 16 hours
  3. washthe mixture was washed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customa fraction obtained from the elution portion with hexane

Sources & evidence

ORD record
ord-b0f6cc823d4a4d049f22f0940cdbfe7f
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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