Pyrazole → HCID 66767292, compound

HRID 1662022Notes

Reaction equation

HRID 1662022 reaction equation
Br[CH2:2][C:3]1[N:7]([CH3:8])[N:6]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:5](=[O:16])[C:4]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[NH:22]1[CH:26]=[CH:25][CH:24]=[N:23]1.[OH-].[K+].CCOC(C)=O>C1COCC1.O>[N:22]1([CH2:2][C:3]2[N:7]([CH3:8])[N:6]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[C:5](=[O:16])[C:4]=2[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:26]=[CH:25][CH:24]=[N:23]1

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 66767121HCID 66767121, compound

Product 1

HCID 66767292HCID 66767292, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(bromomethyl)-2-(4-fluorophenyl)-1-methyl-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate (1.3 g, 3.6 mmol) and 1H-pyrazole (0.25 g, 3.6 mmol) in THF (50 mL) and H2O (1 mL) cooled in an ice-water bath is added solid KOH (0.2 g, 3.6 mmol) in three portions. After the reaction mixture is stirred at RT overnight, the solvent is removed. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (4:1) to give the product (0.87 g, 70% yield). MS (m/z): 345.1 (M+H).

Workup

  1. customthe solvent is removed
  2. customThe residue is purified by silica gel column chromatography
  3. washeluting with PE

Sources & evidence

ORD record
ord-9abe1eb6a8564edabf32dfeffe2bb337
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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