tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → Diethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-propylimidazole-4,5-dicarboxylate

HRID 52950Notes

Reaction equation

HRID 52950 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:8]=1)[CH2:2][CH3:3].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:23][CH:22]=1.CC(C)([O-])C.[K+]>>[C:36]([O:35][C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:8]2[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[N:5]=[C:4]2[CH2:1][CH2:2][CH3:3])=[CH:22][CH:23]=1)=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

4

Reactant 3

HCID 9906257tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 102860151H-Imidazole-4,5-dicarboxylic acid, 2-propyl-, 4,5-diethyl esterHCID 23665647Potassium tert-butoxide

Product 1

HCID 10768304Diethyl 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-propylimidazole-4,5-dicarboxylateYield 89.4%

Procedure

Following a procedure similar to that described in Example 1(a), but using 9.0 g of diethyl 2-propylimidazole-4,5-dicarboxylate (prepared as described in Preparation 12), 12.3 g of t-butyl 4'-bromomethylbiphenyl-2-carboxylate and 4.1 g of potassium t-butoxide as a base, 16.47 g of the title compound were obtained as a viscous oil.

Sources & evidence

ORD record
ord-a99d108736ac4792987c14692938c18b
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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