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

HRID 52887Notes

Reaction equation

HRID 52887 reaction equation
[C:1]([C:9]1[N:10]=[C:11]([CH2:16][CH2:17][CH2:18][CH3:19])[NH:12][C:13]=1[C:14]#[N:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:29]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[C:1]([C:9]1[N:10]=[C:11]([CH2:16][CH2:17][CH2:18][CH3:19])[N:12]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[CH:24][CH:23]=2)[C:13]=1[C:14]#[N:15])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178441735HCID 178441735, compound

Product 1

HCID 190360884-Benzoyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazoleYield 80.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 11(a), but using 1.27 g of 4-benzoyl-2-butyl-5-cyanoimidazole (prepared as described in Preparation 6), 1.74 g of t-butyl 4'-bromomethylbiphenyl-2-carboxylate, 0.69 of potassium carbonate and 20 ml of N,N-dimethylacetamide, and then purifying the product by column chromatography through silica gel, using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, 2.1 g of the title compound were obtained.

Workup

  1. custompurifying the product by column chromatography through silica gel
  2. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-c7a3073e69f24255a6302c6c7094b190
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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