Cesium carbonate → 2-[1-(2,3-Dimethylphenyl)ethyl]-1-(2-methoxybenzyl)-1H-imidazole
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH:19]([C:21]1[NH:22][CH:23]=[CH:24][N:25]=1)[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH3:11][C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=1[CH:19]([C:21]1[N:25]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[O:9][CH3:10])[CH:24]=[CH:23][N:22]=1)[CH3:20]Participants
5
Procedure
1-(Bromomethyl)-2-methoxybenzene (J. Indian Chem. Soc.; 28, 1951, 277; 150 mg, 0.75 mmol) was added to a suspension of the compound of Example 1 (100 mg, 0.5 mmol) and caesium carbonate (406 mg, 1.2 mmol) in acetone (4 ml), under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 18 h. The mixture was filtered and the filtrate was concentrated in vacuo. To the residue was added water (10 ml) and ethyl acetate (10 ml) and the two layers were separated. The aqueous layer was washed with a further portion of ethyl acetate (10 ml) and the combined organic layers were dried (MgSO4) and concentrated in vacuo.
Workup
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
- additionTo the residue was added water (10 ml) and ethyl acetate (10 ml)
- customthe two layers were separated
- washThe aqueous layer was washed with a further portion of ethyl acetate (10 ml)
- dry with materialthe combined organic layers were dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-0018474906e7459bb3e9aeb020ce1925
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592362B2
Reaction notes
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