Sodium hydride → HCID 59276382, compound

HRID 2070869Notes

Reaction equation

HRID 2070869 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:12][CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=[N:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1866731H-Imidazole, 5-(3-bromophenyl)-HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 59276382HCID 59276382, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred solution of 5-(3-bromophenyl)-1H-imidazole (1 g, 4.5 mmol) in anhydrous N,N-dimethylformamide (20 mL) was added sodium hydride (60% in mineral oil, 160 mg, 4.7 mmol) at 0° C., and the mixture was stirred at this temperature for 0.5 h. A solution of (2-(chloromethoxy)ethyl)trimethylsilane (0.9 mL, 5.36 mmol) in N,N-dimethylformamide (5 mL) was added dropwise, and the resulting mixture was stirred at room temperature for 4 h. When the starting material was consumed, the reaction was quenched with water. The mixture was extracted with ethyl acetate, and the combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified on silica gel column (eluting with 5-10% ethyl acetate in petroleum ether) to give 5-(3-bromophenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (1.1 mg, 69.6% yield) as a yellow solid. MS (ESI): m/z 353.0 [M+1]+.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 4 h
  2. customWhen the starting material was consumed
  3. customthe reaction was quenched with water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified on silica gel column (eluting with 5-10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-4777254f066c44a38e095cf3af1cef36
Source dataset
uspto-grants-2012_10
Patent number
US08299056B2

Reaction notes

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