Potassium Carbonate → 4-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

HRID 52884Notes

Reaction equation

HRID 52884 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.[C:28]([C:31]1[N:32]=[C:33]([CH2:38][CH2:39][CH2:40][CH3:41])[NH:34][C:35]=1[C:36]#[N:37])(=[O:30])[CH3:29]>CN(C)C(=O)C.C(OCC)(=O)C>[C:28]([C:31]1[N:32]=[C:33]([CH2:38][CH2:39][CH2:40][CH3:41])[N:34]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:11][CH:10]=2)[C:35]=1[C:36]#[N:37])(=[O:30])[CH3:29]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178441657HCID 178441657, compound

Product 1

HCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazoleYield 45.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

0.87 g of potassium carbonate and 2.4 g of t-butyl 4'-bromomethylbiphenyl-2-carboxylate were added to a solution of 1.2 g of 4-acetyl-2-butyl-5-cyanoimidazole (prepared as described in Preparation 5) in 12 ml of N,N-dimethylacetamide, and the resulting mixture was shirred at room temperature for 3 hours. At the end of this time, the reaction mixture was diluted with 100 ml of ethyl acetate and washed with a saturated aqueous solution of sodium chloride. The aqueous layer was once again extracted with 50 ml of ethyl acetate, and the combined extracts were washed with a saturated aqueous solution of sodium chloride. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.31 g of the title compound.

Workup

  1. washwashed with a saturated aqueous solution of sodium chloride
  2. extractionThe aqueous layer was once again extracted with 50 ml of ethyl acetate
  3. washthe combined extracts were washed with a saturated aqueous solution of sodium chloride
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-d033052598804b7d976daa0bbd288f27
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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