Imidazole → HCID 67230584, compound

HRID 876432Notes

Reaction equation

HRID 876432 reaction equation
[Br:1][C:2]1[C:11]([OH:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1.N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20]>[NH4+].[Cl-].C(Cl)Cl>[Br:1][C:2]1[C:11]([O:12][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH3:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21824657HCID 21824657, compound

Product 1

HCID 67230584HCID 67230584, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

To the product from Step A (3.0 g, 12.6 mmol) was added imidazole (1.89 g, 27.7 mmol) and CH2Cl2 (40 mL). The solution was cooled to 0° C. and then tert-butylchlorodimethylsilane (2.09 g, 13.9 mmol) was added in one portion. The reaction was gradually warmed to ambient temperature over 1 hour then stirred overnight. The mixture was diluted with a saturated aqueous NH4Cl solution (25 mL) and CH2Cl2 (40 mL). The layers were mixed and separated and the organic layer was washed with brine and dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (2 to 20% CH2Cl2/hexanes) to provide 3.36 g (76%) of the desired product as a white solid.

Workup

  1. temperatureThe reaction was gradually warmed to ambient temperature over 1 hour
  2. additionThe layers were mixed
  3. customseparated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (2 to 20% CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-fb5fbb05e8364bb185c8794d196614b3
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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