2-Methylimidazoline → [6-Methoxy-2'-(2-methyl-4,5-dihydro-imidazol-1-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

HRID 456233Notes

Reaction equation

HRID 456233 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23]Br)[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[CH3:26][C:27]1[NH:28][CH2:29][CH2:30][N:31]=1.[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][N:31]2[CH2:30][CH2:29][N:28]=[C:27]2[CH3:26])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 107982-MethylimidazolineHCID 24758Sodium hydrideHCID 66606639(2'-Bromomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 66891914[6-Methoxy-2'-(2-methyl-4,5-dihydro-imidazol-1-ylmethyl)-4'-trifluoromethyl-biphenyl-3-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To (2′-bromomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.070 g, 0.17 mmol) and 2-methyl-2-imidazoline (0.017 g, 0.18 mmol) in DMF (1 mL) at 0° C. was added sodium hydride (60% in mineral oil; 0.011 g, 0.18 mmol), and the reaction was stirred for 2 hours. After work-up with EtOAc, H2O, and citric acid, the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. dry with materialAfter work-up with EtOAc, H2O, and citric acid, the combined organic layers were dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0cfc5c341f3b43a988a7d3f7ae94bf44
Source dataset
uspto-grants-2013_07
Patent number
US08497381B2

Reaction notes

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