Imidazole → HCID 69331800, compound

HRID 351240Notes

Reaction equation

HRID 351240 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:28]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[N:27]=[C:26]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:25]=2)=[CH:20][CH:19]=1>CN(C=O)C>[Si:6]([O:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[N:28]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[N:27]=[C:26]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH:25]=2)=[CH:22][CH:23]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21091021HCID 21091021, compound

Product 1

HCID 69331800HCID 69331800, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (680 mg) and t-butyldimethylsilyl chloride (903 mg) was added successively to a solution of ethyl 5-[4-{2-(hydroxy)ethoxy}phenyl]-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate (1.91 g) in DMF (15 ml) under cooling in an ice bath. After stirring at ambient temperature for 2 hours, the mixture was partitioned between AcOEt and H2O. The oreganic layer was washed with H2O, saturated aqueous sodium chloride solution, dried over MgSO4, concentrated in vacuo. The residual crystals were collected and washed with n-hexane to give ethyl 5-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)-phenyl]-1-(4-methoxyphenyl)-1H-pyrazole-3-carboxylate (2.34 g).

Workup

  1. temperatureunder cooling in an ice bath
  2. customthe mixture was partitioned between AcOEt and H2O
  3. washThe oreganic layer was washed with H2O, saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residual crystals were collected
  7. washwashed with n-hexane

Sources & evidence

ORD record
ord-84f030deed7f4ad9a4690eb293af3a00
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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