Hydrochloric Acid → HCID 23113375, compound

HRID 2102259Notes

Reaction equation

HRID 2102259 reaction equation
[Br:1][C:2]1[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=[C:4]([OH:10])[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>CN(C)C=O>[CH2:22]([O:10][C:4]1[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:2]([Br:1])[N:6]([CH:7]([CH3:9])[CH3:8])[N:5]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178470082HCID 178470082, compound

Product 1

HCID 23113375HCID 23113375, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-bromo-3-hydroxy-1-isopropylpyrazole-4-carboxylate (5.8 g) and potassium carbonate (3.5 g) were suspended in N,N-dimethylformamide (50 mL) and to the stirred suspension was added benzyl bromide (2.76 mL) under ice cooling. The mixture was stirred at room temperature for 6 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid (100 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give 7.7 g of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-734388e1ec3449abbc6311f085b6585c
Source dataset
uspto-grants-2009_08
Patent number
US07576064B2

Reaction notes

Loading…