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

HRID 2080419Notes

Reaction equation

HRID 2080419 reaction equation
C(#N)C.Cl[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[Cl:29])[C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[F:22])(=[O:13])=[O:12])=[CH:7][N:6]=1.[F-:30].[K+]>[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCCl>[Cl:29][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:23]=1[CH:14]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[F:22])[S:11]([C:8]1[CH:9]=[CH:10][C:5]([F:30])=[N:6][CH:7]=1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 522689Potassium FluorideHCID 23114670HCID 23114670, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 2724163Tetraphenylphosphonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an acetonitrile (2 ml) solution of 2-chloro-5-[(3-chloropyridin-4-yl)(2,5-difluorophenyl)methylsulfonyl]pyridine (66 mg, 0.16 mmol) were added potassium fluoride (94 mg, 1.60 mmol) and tetraphenylphosphonium bromide (134 mg, 0.32 mmol). The resulting mixture was heated under reflux for 16 hours. After the reaction mixture was cooled to room temperature, dichloromethane was added thereto. The resulting 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 silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=17:3 eluate is concentrated under reduced pressure to give the title compound (4.5 mg, 0.011 mmol, 7%) as a white solid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 16 hours
  3. washThe resulting 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. customThe fraction obtained from the hexane
  8. concentrationethyl acetate=17:3 eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-37a68462373a4a0c9c17184dbdc787dc
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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