Phthalimide potassium salt → N-(2-(4-Bromopyrazol-1-yl)ethyl)phthalimide

HRID 2366840Notes

Reaction equation

HRID 2366840 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8]Cl)[CH:6]=1.[C:10]1(=[O:20])[NH:14][C:13](=[O:15])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.[K]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][N:14]2[C:10](=[O:20])[C:11]3[C:12](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:13]2=[O:15])[CH:6]=1

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 518920744-Bromo-1-(2-chloroethyl)-1H-pyrazole

Product 1

HCID 53216871N-(2-(4-Bromopyrazol-1-yl)ethyl)phthalimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4-bromo-1-(2-chloroethyl)-1H-pyrazole (for a preparation see Intermediate 29) (120 mg, 0.573 mmol) was mixed with potassium phthalimide (159 mg, 0.859 mmol), dissolved in N,N-Dimethylformamide (DMF) (4 mL) and stirred under nitrogen at 120° C. for 20 hours. The reaction was left to cool to room temperature and the product was partitioned between distilled water (20 mL) and EtOAc (60 mL). The aqueous layer was extracted with EtOAc (60 mL) and the organic fractions were combined, washed (brine, 30 mL), dried (MgSO4), filtered and evaporated to dryness to give a white solid. The product was purified on a 25+S Biotage silica column, eluting with cyclohexane:EtOAc (1:0 to 7:3). Product-containing fractions were evaporated to dryness to give a white solid (85 mg).

Workup

  1. waitThe reaction was left
  2. temperatureto cool to room temperature
  3. customthe product was partitioned
  4. distillationbetween distilled water (20 mL) and EtOAc (60 mL)
  5. extractionThe aqueous layer was extracted with EtOAc (60 mL)
  6. washwashed (brine, 30 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customto give a white solid
  11. customThe product was purified on a 25+S Biotage silica column
  12. washeluting with cyclohexane:EtOAc (1:0 to 7:3)
  13. customProduct-containing fractions were evaporated to dryness

Sources & evidence

ORD record
ord-49bb48e82eff4ac19c8a65e47e4f6d93
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

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