Sodium hydride → HCID 86689689, compound

HRID 1775839Notes

Reaction equation

HRID 1775839 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:29][Si:30]([CH3:37])([CH3:36])[CH2:31][CH2:32][O:33][CH2:34]Cl>CN(C=O)C.C1COCC1.CC(=O)OCC>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:34][O:33][CH2:32][CH2:31][Si:30]([CH3:37])([CH3:36])[CH3:29])[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 89620321HCID 89620321, compound

Product 1

HCID 86689689HCID 86689689, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-bromophenyl)-5-(4-(heptyloxy)phenyl)-1H-imidazole (370 g, 900 mmol) in DMF (4 ml) was added NaH (40 mg, 980 mmol). After 2 h, 2-(trimethylsilyl)ethoxymethyl chloride (160 g, 990 mmol) in THF (2 ml) was added dropwise and reaction mixture was stirred overnight. The reaction mixture was diluted with EA and washed with aq. NaHCO3. The organics were dried over MgSO4, filtered, and the solvent was removed under reduced pressure. The crude product was purified by chromatography (EA/hexane) to afford 32 mg (65%) of 2-(4-bromophenyl)-5-(4-(heptyloxy)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole as a tan solid. LCMS-ESI (m/z) calculated for C28H39BrN2O2Si: 542.2. found 543.3 [M+H]+, tR=3.35 min (Method 8).

Workup

  1. customreaction mixture
  2. washwashed with aq. NaHCO3
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by chromatography (EA/hexane)

Sources & evidence

ORD record
ord-41c9da9779844917b37035d284d10d04
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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