Potassium Carbonate → [3-Chloro-5-(2,4-difluorophenoxyl)pyrazin-2-yl]-(2-chlorophenyl)methanone

HRID 230202Notes

Reaction equation

HRID 230202 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:15]([Cl:16])=[N:14][C:13](Cl)=[CH:12][N:11]=1)=[O:9].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[OH:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:16][C:15]1[C:10]([C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[O:9])=[N:11][CH:12]=[C:13]([O:26][C:20]2[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=2[F:18])[N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230512,4-DifluorophenolHCID 59812791(2-Chlorophenyl)-(3,5-dichloropyrazin-2-yl)methanone

Product 1

HCID 59812803[3-Chloro-5-(2,4-difluorophenoxyl)pyrazin-2-yl]-(2-chlorophenyl)methanoneYield 88.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a dimethylformamide, i.e., DMF, (25 mL) solution of (2-chlorophenyl)-(3,5-dichloropyrazin-2-yl)methanone (2.1 g, 7.3 mmol, 1.0 eq) under nitrogen was added 2,4-difluorophenol (0.7 mL, 7.3 mmol, 1.0 eq) and potassium carbonate (1.21 g, 8.76 mmol, 1.2 eq). The resulting mixture was stirred overnight at room temperature and then concentrated. The residue was dissolved in dichloromethane and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated to give a crude oil which was purified via a chromatography using dichloromethane/hexanes (1:1) as the eluent to give [3-chloro-5-(2,4-difluorophenoxyl)pyrazin-2-yl]-(2-chlorophenyl)methanone (2.46 g, 6.45 mmol, 88% yield). Mass spec. M+1=382.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude oil which
  8. customwas purified via a chromatography

Sources & evidence

ORD record
ord-bb3a570e205547f78d2f4b6c934e3a33
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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