Imidazole → HCID 21717163, compound

HRID 1600925Notes

Reaction equation

HRID 1600925 reaction equation
N1C=CN=C1.[Br:6][C:7]1[CH:24]=[CH:23][C:10]([O:11][CH2:12][CH:13]([OH:22])[CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:9][CH:8]=1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[Cl-].[Na+]>CN(C)C=O.CN(C1C=CC=CN=1)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH:13]([O:22][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])[CH2:14][CH2:15][C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:23][CH:24]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 5234Sodium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 21717167HCID 21717167, compound

Product 1

HCID 21717163HCID 21717163, compound

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Imidazole (0.73 g) and dimethylaminopyridine (10 mg) was added to a solution of (±)-1-(4-bromophenoxy)-4-(3-pyridyl)-2-butanol (2.20 g) in dimethylformamide (15 ml). When the mixture was homogeneous solid tert-butyldimethylsilyl chloride was added and the solution stirred for 26 hours. A saturated aqueous solution of sodium chloride (200 ml) was added and the mixture extracted with ether (3×100 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the sub-title compound as an oil (2.75 g).

Workup

  1. additionwas added
  2. extractionthe mixture extracted with ether (3×100 ml)
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0789cb8b695540f2b749ef515e125f5a
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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