Dimethylformamide → 1-[(4-Bromo-2-fluorophenyl)methyl]-5-carbomethoxy-4-ethyl-2-n-propylimidazole

HRID 1078033Notes

Reaction equation

HRID 1078033 reaction equation
[C:1]([C:5]1[NH:9][C:8]([CH2:10][CH2:11][CH3:12])=[N:7][C:6]=1[CH2:13][CH3:14])([O:3][CH3:4])=[O:2].[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[C:18]([F:24])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(OCC)(=O)C>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][N:9]2[C:5]([C:1]([O:3][CH3:4])=[O:2])=[C:6]([CH2:13][CH3:14])[N:7]=[C:8]2[CH2:10][CH2:11][CH3:12])=[C:18]([F:24])[CH:17]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 178440058HCID 178440058, compound

Product 1

HCID 158190481-[(4-Bromo-2-fluorophenyl)methyl]-5-carbomethoxy-4-ethyl-2-n-propylimidazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-Carbomethoxy-4-ethyl-2-n-propylimidazole (U.S. Pat. No. 5,137,902) (10.62 g, 54 mmol, 1 eq), 1-bromo-4-bromomethyl-3-fluorobenzene (19.58 g, 54 mmol, 1 eq), potassium carbonate (7.48 g, 54 mmol, 1 eq), and DMF (200 mL) were mixed and stirred overnight at room temperature. Ethyl acetate was added (500 mL) and the mixture was washed with water (3×300 mL). The ethyl acetate layer was dried (MgSO4), and the solvent removed in vacuo to yield 25.42 g of an oil. Flash chromatography in 75:25 to 65:35 hexanes/ethyl acetate yielded 13.65 g of product as an amber oil. NMR (CDCl3) δ 7.35-7.22 (m, 1H); 7.22-7.10 (m, 1H); 6.45 (t, 1H, J=7Hz); 5.49 (s, 2H); 3.78 (s, 3H); 2.90 (q, 2H, J=7Hz); 2.59 (t, 2H, J=7Hz); 1.70 (t of q, 2H, J=7,7Hz); 1.35-1.15 (m, 3H); 0.95 (t, 3H, J=7Hz). ##STR48##

Workup

  1. washthe mixture was washed with water (3×300 mL)
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-dfe9b4bb95ab4d87be65f5f86d4ca0b1
Source dataset
uspto-grants-1996_08
Patent number
US05545651

Reaction notes

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