Imidazole → HCID 21877099, compound

HRID 353102Notes

Reaction equation

HRID 353102 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[C:11]([CH2:20][CH3:21])=[N:12][N:13]([CH2:17][CH2:18][OH:19])[C:14]=2[CH2:15][CH3:16])[CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>CN(C)C=O>[Si:31]([O:19][CH2:18][CH2:17][N:13]1[C:14]([CH2:15][CH3:16])=[C:10]([S:9][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[C:6]([Br:8])[CH:5]=2)[C:11]([CH2:20][CH3:21])=[N:12]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10274527HCID 10274527, compound

Product 1

HCID 21877099HCID 21877099, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 2-{4-[(3,5-dibromophenyl)sulfanyl]-3,5-diethyl-1H-pyrazol-1-yl}ethanol (1.3 g, 3 mmol) (Example 93) in dimethylformamide (3 ml) was treated with imidazole (270 mg, 4 mmol) and tert-butyl(chloro)dimethylsilane (500 mg, 3.3 mmol) and stirred at 20° C. for 15 hours. The mixture was partitioned between diethyl ether (70 ml) and citric acid solution (5% weight:volume in water, 150 ml). The aqueous layer was further extracted with diethyl ether (70 ml) and the combined organic layers were washed with brine (2×70 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel eluting with pentane:dichloromethane (1:1, by volume) to provide the title compound (1.2 g) as a colourless oil.

Workup

  1. customThe mixture was partitioned between diethyl ether (70 ml) and citric acid solution (5% weight:volume in water, 150 ml)
  2. extractionThe aqueous layer was further extracted with diethyl ether (70 ml)
  3. washthe combined organic layers were washed with brine (2×70 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by flash chromatography on silica gel eluting with pentane:dichloromethane (1:1, by volume)

Sources & evidence

ORD record
ord-ee566148012346f1bc3d1aacc894d9b5
Source dataset
uspto-grants-2004_06
Patent number
US06750230B2

Reaction notes

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