Imidazole → HCID 66691631, compound

HRID 1773648Notes

Reaction equation

HRID 1773648 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][OH:10].N1C=CN=C1.Cl[Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19].O>CN(C)C=O.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][O:10][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 27733492-Bromo-5-fluorobenzyl alcohol

Product 1

HCID 66691631HCID 66691631, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 5.00 g (24.4 mmol) (2-bromo-5-fluorophenyl)methanol in 100 mL N,N-dimethylformamide were added 2.49 g imidazole, 6.20 mL chloro(triisopropyl)silane, 1.49 g N,N-dimethylpyridin-4-amine and the mixture was stirred at 23° C. for 2 days. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvent the residue was purified by chromatography to give 8.17 g (93%) of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and removal of the solvent the residue
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-055b51b0814146419bf544a48a508c79
Source dataset
uspto-grants-2016_02
Patent number
US09255100B2

Reaction notes

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