Sodium hydride → HCID 23023146, compound

HRID 2217125Notes

Reaction equation

HRID 2217125 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:7]=[CH:6][C:5]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].F[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N+:28]([O-:30])=[O:29].OS([O-])(=O)=O.[K+]>>[CH2:9]([N:8]1[C:4]([NH:3][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[N+:28]([O-:30])=[O:29])=[C:5]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:6]=[N:7]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 516920Potassium bisulfateHCID 785810ethyl 5-amino-1-benzyl-1H-pyrazole-4-carboxylate

Product 1

HCID 23023146HCID 23023146, compoundYield 76%

Procedure

Sodium hydride (60% dispersion in oil, 520 mg, 13 mmol) was added portionwise to a suspension of ethyl 5-amino-1-benzylpyrazole-4-carboxylate (2.2 g, 9 mmol) in anhydrous THP (30 ml) at 0° C. The mixture was allowed to warm to room temperature and stirred for 2 h then 1-fluoro-2-nitrobenzene (1.26 g, 9 mmol) was added and the resultant deep purple suspension was stirred at room temperature for 18 h. 1 M KHSO4 was added to quench the reaction and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and the solution was washed with 0.3 M KHSO4, sat. NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant 75% pet. ether/25% ethyl acetate) to yield ethyl 1-benzyl-5-(2′-nitrophenylamino)pyrazole-4-carboxylate (2.5 g, 76%).

Workup

  1. stirringthe resultant deep purple suspension was stirred at room temperature for 18 h
  2. customto quench
  3. customthe reaction
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washthe solution was washed with 0.3 M KHSO4, sat. NaHCO3 and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel (eluant 75% pet. ether/25% ethyl acetate)

Sources & evidence

ORD record
ord-ebf52a54d1464590b7560c2a5da0b72f
Source dataset
uspto-grants-2008_08
Patent number
US07407949B2

Reaction notes

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