Hydrochloric Acid → methyl 4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzoate

HRID 507953Notes

Reaction equation

HRID 507953 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1.Cl>CN(C)C=O>[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:7]([CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 231573073-tert-butyl-5-(2-phenylethyl)-1H-pyrazole

Product 1

HCID 23157206methyl 4-{[3-tert-butyl-5-(2-phenylethyl)-1H-pyrazol-1-yl]methyl}benzoateYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-tert-butyl-5-(2-phenylethyl)-1H-pyrazole (1.57 g, 6.87 mmol), sodium hydride (60% in oil, 280 mg, 7 mmol), and N,N-dimethylformamide (15 mL) was added methyl 4-(bromomethyl)benzoate (2.29 g, 10.0 mmol) at room temperature, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 1 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane) to give the title compound (1.75 g, yield 68%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-61db6c768dab4d4bb7d1942562db2fee
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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