Imidazole → HCID 22335733, compound

HRID 586649Notes

Reaction equation

HRID 586649 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:9][C:10]1([CH3:27])[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]2[CH:15]=[C:14](/[C:22](/[CH3:26])=[CH:23]\[CH2:24][OH:25])[CH:13]=[CH:12][C:11]1=2.N1C=CN=C1>CN(C=O)C>[C:4]([Si:1]([CH3:3])([CH3:2])[O:25][CH2:24]/[CH:23]=[C:22](\[C:14]1[CH:13]=[CH:12][C:11]2[C:10]([CH3:27])([CH3:9])[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=2[CH:15]=1)/[CH3:26])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 10934165HCID 10934165, compound

Product 1

HCID 22335733HCID 22335733, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylsilyl chloride (2.7 g, 17.5 mmol) was added to the solution of Intermediate 2 (3 g, 11.6 mmol) and imidazole (1.6 g, 23.2 mmol) in 10 mL of DMF. The mixture was then stirred for 16 h at room temperature. After quenching with water, the mixture was extracted with ether (3×10 mL), washed with brine (1×10 mL), dried (MgSO4) and concentrated to give a crude brown oil. The crude product was purified by flash chromatography using 10% EtOAc in hexane to give the title compound (3 g, 70% yield) as a colorless oil:

Workup

  1. customAfter quenching with water
  2. extractionthe mixture was extracted with ether (3×10 mL)
  3. washwashed with brine (1×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto give a crude brown oil
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-974055f1d68f4b9a95f8f42a90b13ea7
Source dataset
uspto-grants-2005_08
Patent number
US06936636B2

Reaction notes

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