Imidazole → HCID 137329040, compound

HRID 1631933Notes

Reaction equation

HRID 1631933 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](CO)=[N:6][CH:7]=1.[C:10]([Si:14](Cl)(C)C)([CH3:13])([CH3:12])[CH3:11].N1C=CN=[CH:19]1.C([O:26][CH2:27][CH3:28])(=O)C>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:27]([CH3:28])([CH3:19])[O:26][SiH2:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 137329040HCID 137329040, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (5-bromo-pyridin-2-yl)-methanol (500 mg) in DMF (2 ml) at room temperature, was added tert-butyl-chloro-dimethyl-silane (0.48 g) and imidazole (0.36 g). After overnight stirring, ethyl acetate was added followed by water and mixture extracted 3 times with ethyl acetate. The organic layer was separated; washed with water and brine solution, then dried and concentrated to afford 800 mg of the title compound. ESI mass spectrum: [M]+=302.

Workup

  1. extractionextracted 3 times with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water and brine solution
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ccb8cc362d09452ead16a4c1f88a7c8e
Source dataset
uspto-grants-2014_07
Patent number
US08791272B2

Reaction notes

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