Dimethylformamide → HCID 23157275, compound

HRID 507964Notes

Reaction equation

HRID 507964 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([OH:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1.[C:23](=[O:26])([O-])[O-].[K+].[K+].CN(C)[CH:31]=[O:32]>O>[C:1]([C:5]1[CH:9]=[C:8]([O:10][CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)[N:7]([CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:23]([O:32][CH3:31])=[O:26])=[CH:15][CH:14]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178441205HCID 178441205, compound

Product 1

HCID 23157275HCID 23157275, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-tert-butyl-5-hydroxy-1H-pyrazole (5.00 g, 35.7 mmol), methyl 4-(bromomethyl)benzoate (17.2 g, 74.9 mmol), potassium carbonate (10.5 g, 76.0 mmol) and N,N-dimethylformamide (50 mL) was stirred overnight at 60° C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane) to give the title compound (6.90 g, yield 44%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c21fa001d4e245a7a85597be5965f820
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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