Acetone → HCID 67855017, compound

HRID 1655181Notes

Reaction equation

HRID 1655181 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=2)[C:7]=1[CH:8]=[CH:9][C:10](O)=[O:11])#[N:2].C(=O)([O-])[O-].[K+].[K+].BrC[C:32]([O:34][C:35]([CH3:38])(C)C)=[O:33].[CH3:39][C:40]([CH3:42])=[O:41]>>[C:1]([C:3]1[CH:4]=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:21])([F:23])[F:22])=[CH:15][N:14]=2)[C:7]=1[CH:8]=[CH:9][C:10]([O:41][C:40]([C:32]([O:34][CH2:35][CH3:38])=[O:33])([CH3:42])[CH3:39])=[O:11])#[N:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 54321359HCID 54321359, compound

Product 1

HCID 67855017HCID 67855017, compound

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 0.4 gram (0.001 mole) of 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylic acid in 25 mL of acetone were added in succession 0.2 gram (0.001 mole) of potassium carbonate and 0.2 gram (0.001 mole) of 1,1-dimethylethyl bromoacetate. Upon completion of the addition, the reaction mixture was stirred at 25° C. for 25 minutes, and then it was heated to reflux where it was stirred for one hour. After this time, the reaction mixture was cooled and concentrated under reduced pressure to a residue. The residue was shaken with methylene chloride and water. The organic layer was washed with water and then dried with calcium sulfate. The mixture was filtered through silica gel. The silica gel filter pad was washed with petroleum ether. The combined filtrates were concentrated under reduced pressure, yielding 0.5 gram of 1,1-dimethylethoxycarbonylmethyl 3-[4-cyano-1-(3-chloro-5-trifluoromethylpyridin-2-yl)-1H-pyrazol-5-yl]acrylate; m.p. 110° -112° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition
  2. temperatureit was heated
  3. temperatureto reflux where it
  4. stirringwas stirred for one hour
  5. temperatureAfter this time, the reaction mixture was cooled
  6. concentrationconcentrated under reduced pressure to a residue
  7. stirringThe residue was shaken with methylene chloride and water
  8. washThe organic layer was washed with water
  9. dry with materialdried with calcium sulfate
  10. filtrationThe mixture was filtered through silica gel
  11. filtrationThe silica gel filter pad
  12. washwas washed with petroleum ether
  13. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-52892f82830043959792664db182b51c
Source dataset
uspto-grants-1993_10
Patent number
US05250504

Reaction notes

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