Sodium hydride → HCID 57580360, compound

HRID 251743Notes

Reaction equation

HRID 251743 reaction equation
[H-].[Na+].[Br:3][C:4]1[NH:5][CH:6]=[C:7]([Br:9])[N:8]=1.[CH3:10][Si:11]([CH2:14][CH2:15][O:16][CH2:17]Cl)([CH3:13])[CH3:12]>C1COCC1>[Br:3][C:4]1[N:5]([CH2:17][O:16][CH2:15][CH2:14][Si:11]([CH3:13])([CH3:12])[CH3:10])[CH:6]=[C:7]([Br:9])[N:8]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178419462HCID 178419462, compound

Product 1

HCID 57580360HCID 57580360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (60%, 1.2 eq) was added portionwise to a solution of 2,4-dibromoimidazole (1 eq.) in THF at 0° C. After 1 hr, SEM-Cl (1.2 eq.) was added and the mixture was stirred at RT for 12 hr. The reaction was carefully quenched with H2O and the aqueous phase was extracted with EtOAc (3×). The combined organic phase was dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 5-33% EtOAc/pentane yielded the title compound as an oil. 1H NMR (300 MHz, CDCl3) δ: 7.09 (1H, s), 5.22 (2H, s), 3.54 (2H, t, J=8.1 Hz), 0.92 (2H, t, J=8.1 Hz), 0.00 (9H, s). MS (ES) C9H16Br2N2OSi requires: 354/356/358, found: 355/357/359 (M+H)+.

Workup

  1. customThe reaction was carefully quenched with H2O
  2. extractionthe aqueous phase was extracted with EtOAc (3×)
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography on silica gel eluting with 5-33% EtOAc/pentane

Sources & evidence

ORD record
ord-c512977224364869a1cc69352b016d31
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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