Imidazole → HCID 58014000, compound

HRID 2357899Notes

Reaction equation

HRID 2357899 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:13]=[C:6]2[C:7]([CH2:11][OH:12])=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].O>CN(C=O)C>[Si:21]([O:12][CH2:11][C:7]1[C:6]2[N:5]([N:4]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:13]=2)[CH:10]=[CH:9][CH:8]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 59389331HCID 59389331, compound

Product 1

HCID 58014000HCID 58014000, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 64 (5.17 g, crude product) was dissolved in DMF (100 mL). To this solution, imidazole (4.89 g) and t-butyldimethylsilyl chloride (4.33 g) were added and the mixture was stirred at room temperature for 1.5 hours. Subsequently, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent and subsequent purification by silica gel column chromatography (hexane:ethyl acetate=9:1) afforded the title compound as a yellow oil (3.42 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customEvaporation of the solvent and subsequent purification by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f315cbb500dd4fd28e83a5e8fc40e0fb
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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