Ethyl Acetate → HCID 57736453, compound

HRID 1641680Notes

Reaction equation

HRID 1641680 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9](Cl)[C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])=[CH:4][N:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2[F:17])[S:26][C:23]2[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=2)=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 677894-FluorothiophenolHCID 57736409HCID 57736409, compound

Product 1

HCID 57736453HCID 57736453, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-bromo-5-[chloro(2,5-difluorophenyl)methyl]-4-methylpyridine (6.44 g, 19.4 mmol) in N,N-dimethylformamide (100 ml), 4-fluorobenzenethiol (2.06 ml, 19.4 mmol), and then potassium carbonate (2.94 g, 21.3 mmol) were added in an argon atmosphere, at 0° C., and the mixture was stirred for 1 hour at room temperature. Ethyl acetate and water were added to the reaction mixture, the organic layer was separated, and then the organic layer was washed with saturated aqueous sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution of hexane:ethyl acetate=30:1 was concentrated under reduced pressure, to obtain the title compound (8.20 g, 19.3 mmol, 100%) as a pale brown solid.

Workup

  1. customthe organic layer was separated
  2. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe fraction obtained from an elution of hexane
  7. concentrationethyl acetate=30:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d3a7c04cfd0b45a9a5450945c9fd4431
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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