Cesium carbonate → ethyl 3-(1-(4-bromobenzyl)-5-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate

HRID 1848699Notes

Reaction equation

HRID 1848699 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]2[NH:7][C:8]([CH2:10][C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Br)=[CH:30][CH:29]=1>CN(C=O)C>[Br:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:9]2[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:20]=[CH:19][C:6]=3[N:7]=[C:8]2[CH2:10][C:11]([CH3:17])([CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:30][CH:29]=1.[Br:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:7]2[C:6]3[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[N:9]=[C:8]2[CH2:10][C:11]([CH3:17])([CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 685274-Bromobenzyl bromideHCID 178471315HCID 178471315, compound

Product 2

HCID 90410153ethyl 3-(1-(4-bromobenzyl)-6-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoateYield 23%HCID 90410194ethyl 3-(1-(4-bromobenzyl)-5-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoateYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100 mL round-bottomed flask were added a stir bar, ethyl 3-(5-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (1.5 g, 5.4 mmol), DMF (19 mL), cesium carbonate (3.5 g, 11 mmol), and 4-bromobenzyl bromide (1.4 g, 5.4 mmol). After 12 h, the mixture was partitioned between water (100 mL) and EtOAc (50 mL). The aqueous layer was extracted with EtOAc (50 mL×3). The combined organic layers were dried with sodium sulfate, filtered, and concentrated to dryness. The residue was subjected to FCC to give ethyl 3-(1-(4-bromobenzyl)-6-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (550 mg, 23%) and ethyl 3-(1-(4-bromobenzyl)-5-methoxy-1H-benzo[d]imidazol-2-yl)-2,2-dimethylpropanoate (620 mg, 26%).

Workup

  1. additionTo a 100 mL round-bottomed flask were added a stir bar
  2. customthe mixture was partitioned between water (100 mL) and EtOAc (50 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (50 mL×3)
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c24633cf61a343f18d57c53f75c9180e
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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