Sodium hydride → methyl 4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzoate

HRID 507969Notes

Reaction equation

HRID 507969 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1>CN(C)C=O.O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 1369123,5-Di-t-butylpyrazoleHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 23157342methyl 4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzoateYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3,5-di-tert-butyl-1H-pyrazole (1.00 g, 5.55 mmol) in N,N-dimethylformamide (15 mL) was added sodium hydride (60% in oil, 0.27 g, 6.8 mmol) under ice-cooling. After completion of hydrogen generation, methyl 4-(bromomethyl)benzoate (1.40 g, 6.11 mmol) was added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water, and dried to give the title compound (1.78 g, yield 98%) as colorless crystals.

Workup

  1. temperaturecooling
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-c643fa32768a4893a3589e6b72156472
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…