Sodium hydride → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-propionylimidazole-5-carbonitrile

HRID 52922Notes

Reaction equation

HRID 52922 reaction equation
[CH2:1]([C:5]1[NH:6][C:7]([C:14]#[N:15])=[C:8]([C:10](=[O:13])[CH2:11][CH3:12])[N:9]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:25]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1.[H-].[Na+]>CN(C)C(=O)C>[C:33]([O:32][C:30]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18]([CH2:17][N:6]2[C:7]([C:14]#[N:15])=[C:8]([C:10](=[O:13])[CH2:11][CH3:12])[N:9]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:19][CH:20]=1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 178441752HCID 178441752, compound

Product 1

HCID 190361561-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-4-propionylimidazole-5-carbonitrileYield 86.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 45(a) but using 0.923 g of 2-butyl-4-propionylimidazole-5-carbonitrile (prepared as described in Preparation 25), 1.56 g of t-butyl 4'-(bromomethyl)biphenyl-2-carboxylate and 196 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) in 20 ml of N,N-dimethylacetamide, 1.84 g of the title compound were obtained as a viscous oil.

Sources & evidence

ORD record
ord-fb859191724b4978ae911890cceaaea0
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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