Benzyl Bromide → HCID 67325415, compound

HRID 1397456Notes

Reaction equation

HRID 1397456 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]1([C:15]2[NH:19][N:18]=[C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH2:1]([N:19]1[C:15]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:16][C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 178468617HCID 178468617, compound

Product 1

HCID 67325415HCID 67325415, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (696 mg, 4.01 mmol) was added to ethyl 5-phenyl-1H-pyrazole-3-carboxylate (880 mg, 4.1 mmol) and potassium carbonate (562 mg, 4.01) in DMF (8 mL). The reaction was stirred for several h and then diluted with water. The mixture was washed several times with ethyl acetate and the combine extracts were dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified on ISCO using 0-100% ethyl acetate/hexane gradient to give ethyl 1-benzyl-5-phenyl-1H-pyrazole-3-carboxylate (1.3 g, quantitative). MS (ESI) m/z: Calculated for C19H18N2O2: 306.14. found: 307.1 (M+H)+.

Workup

  1. washThe mixture was washed several times with ethyl acetate
  2. dry with materialthe combine extracts were dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified on ISCO

Sources & evidence

ORD record
ord-c986d43d98d84d789689fa0a0432da0d
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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