Methyl 4'-(bromomethyl)biphenyl-2-carboxylate → HCID 19815442, compound

HRID 847111Notes

Reaction equation

HRID 847111 reaction equation
[CH2:1]([C:4]1[NH:5][C:6]([C:13]([O:15][CH3:16])=[O:14])=[C:7]([C:9]([O:11][CH3:12])=[O:10])[N:8]=1)[CH2:2][CH3:3].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([O:33][CH3:34])=[O:32])=[CH:21][CH:20]=1>>[C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:8]2[C:7]([C:9]([O:11][CH3:12])=[O:10])=[C:6]([C:13]([O:15][CH3:16])=[O:14])[N:5]=[C:4]2[CH2:1][CH2:2][CH3:3])=[CH:24][CH:23]=1)([O:33][CH3:34])=[O:32]

Participants

3

Reactant 2

HCID 11012181Methyl 4'-(bromomethyl)biphenyl-2-carboxylateHCID 15222105Dimethyl 2-propyl-1H-imidazole-4,5-dicarboxylate

Product 1

HCID 19815442HCID 19815442, compoundYield 97.6%

Procedure

2-n-Propyl-4,5-dicarbomethoxyimidazole (2.00 g, 8.8 mmol, 1 eq.) was alkylated with 4'-bromomethyl-2-carbomethoxybiphenyl (2.70 g, 8.8 mmol, 1 eq.) by the procedure described in Example 1, Part A. Obtained 3.87 g of a yellow oil which was suitable for further transformation. NMR (DMSO-d6): δ7.84-7.22 (m, 4H); 7.22 (d, 2H, J=9 Hz); 7.13 (d, 2H, J=9 Hz); 5.50 (s, 2H); 3.77 (s, 3H); 3.75 (s, 3H); 3.55 (s, 3H); 2.67 (t, 2H, J=7 Hz); 1.67 (t of q, 2H, J=7,7 Hz); 0.88 (t, 3H, J=7 Hz).

Sources & evidence

ORD record
ord-dd31c38f322445e7a7fc5c538ff4776b
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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