Imidazole → HCID 14350138, compound

HRID 414284Notes

Reaction equation

HRID 414284 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH2:9][C:10]#[CH:11])=[CH:4][CH:3]=1.N1C=CN=C1.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24])[CH2:9][C:10]#[CH:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 10955231HCID 10955231, compound

Product 1

HCID 14350138HCID 14350138, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution containing 19 g (84.5 mmol) of the semi-purified reaction product of Example 1 dissolved in 50 ml of DMF was cooled to 0° C. (ice bath) and 12.9 g (190 mmol) of imidazole was added in one portion. The reaction mixture was stirred 10 minutes until all the imidazole dissolved and then was added in one portion 14.3 g (95 mmol) of t-butyldimethylchlorosilane. After stirring for 5 minutes, the ice bath was removed and the reaction mixture was stirred for an additional 2 hr. at R.T. The reaction was then poured into 500 ml of ether and washed 3× with 50 cc of H2O and 1× with 100 ml of brine. The organic layer was then separated, dried (MgSO4), and removal of all solvent yielded 29.32 g of crude product. Separation by reverse phase HPLC (gradient elution with acetonitrile-water) yielded 9.1 g of the titled product.

Workup

  1. additionwas added in one portion
  2. dissolutiondissolved
  3. customthe ice bath was removed
  4. stirringthe reaction mixture was stirred for an additional 2 hr
  5. customat R.T
  6. additionThe reaction was then poured into 500 ml of ether
  7. washwashed 3× with 50 cc of H2O and 1× with 100 ml of brine
  8. customThe organic layer was then separated
  9. customdried
  10. custom(MgSO4), and removal of all solvent
  11. customyielded 29.32 g of crude product
  12. customSeparation
  13. washby reverse phase HPLC (gradient elution with acetonitrile-water)

Sources & evidence

ORD record
ord-3284312aae444e24a22847c388c8b449
Source dataset
uspto-grants-1988_12
Patent number
US04791133

Reaction notes

Loading…