Sodium hydride → HCID 90460857, compound

HRID 2202120Notes

Reaction equation

HRID 2202120 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[H-].[Na+].Cl[CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178470398HCID 178470398, compound

Product 1

HCID 90460857HCID 90460857, compoundYield 52.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 4-bromo-1H-imidazole-5-carboxylate (400 mg, 1.83 mmol, 1.00 equiv) in N,N-dimethylformamide (2 mL) was added sodium hydride (100 mg, 4.17 mmol, 1.00 equiv) in portions. The reaction was stirred at room temperature for 20 min then [2-(chloromethoxy)ethyl]trimethylsilane (300 mg, 1.80 mmol, 1.00 equiv) was added. The resulting solution was stirred at room temperature for 5 h and then diluted with 50 mL of ethyl acetate. The mixture was washed with 3×10 mL of brine then the organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified on a silica gel column eluted with 0-10% of ethyl acetate in petroleum ether to give 330 mg (52%) of ethyl 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-5-carboxylate as a colorless oil. 1H-NMR (300 MHz, CDCl3): δ 7.69 (s, 1H), 5.67 (s, 2H), 4.43-4.36 (m, 2H), 3.58 (t, J=10.8 Hz, 2H), 1.45-1.40 (m, 3H), 0.94 (t, J=10.8 Hz, 2H), 0.05 (s, 9H) ppm.

Workup

  1. stirringThe resulting solution was stirred at room temperature for 5 h
  2. washThe mixture was washed with 3×10 mL of brine
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column
  6. washeluted with 0-10% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-e8e18a0b6faa4b5eb1d153eff4f08dce
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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