Water → HCID 22320113, compound

HRID 497991Notes

Reaction equation

HRID 497991 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([NH2:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1.Br[C:15]1[C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([F:25])[C:18]([F:26])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(O)(=O)C>[F:25][C:19]1[C:18]([F:26])=[CH:17][CH:16]=[C:15]([NH:7][C:5]2[N:4]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=3)[N:3]=[C:2]([CH3:1])[CH:6]=2)[C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7351323-Methyl-1-(pyridin-2-yl)-1H-pyrazol-5-amineHCID 22320256Methyl 6-bromo-2,3-difluorobenzoate

Product 1

HCID 22320113HCID 22320113, compoundYield 8%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazol-5-ylamine (6.16 g, 35.4 mmol), methyl 6-bromo-2,3-difluorobenzoate (8.11 g, 32.3 mmol), copper acetate (II) (0.49 g, 2.7 mmol) and potassium carbonate (4.46 g, 323 mmol) in N,N-dimethylformamide (30 mL) was heated under reflux for 1 hour under an argon atmosphere, and the solution was allowed to cool to room temperature and poured into water. The solution was made weakly acidic by the addition of acetic acid, and organic matter was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1) to give the title compound (0.86 g, 8% yield).

Workup

  1. temperatureunder reflux for 1 hour under an argon atmosphere
  2. extractionwas extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-2360441562e24a438d32577f5a5b4368
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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