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

HRID 52932Notes

Reaction equation

HRID 52932 reaction equation
[C:1]([C:6]1[N:7]=[C:8]([CH2:13][CH2:14][CH3:15])[NH:9][C:10]=1[C:11]#[N:12])(=[O:5])[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:9]2[C:10]([C:11]#[N:12])=[C:6]([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[N:7]=[C:8]2[CH2:13][CH2:14][CH3:15])=[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 178450364HCID 178450364, compound

Product 1

HCID 190361591-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-4-butyryl-2-propylimidazole-5-carbonitrileYield 72.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Following a procedure similar to that described in Example 45(a), but using 1.026 g of 4-butyryl-2-propylimidazole-5-carbonitrile (prepared as described in Preparation 28), 1.91 g of t-butyl 4'-(bromomethyl)biphenyl-2-carboxylate and 0.209 g of sodium hydride (as a 55% w/w dispersion in mineral oil) in 20 ml of N,N-dimethylacetamide, 1.70 g of the title compound were obtained as a viscous oil.

Sources & evidence

ORD record
ord-bf9520a2b49148438c24c1022588f128
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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