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Cesium carbonate → 5-Bromo-4-chloro-2-ethyl-1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-benzimidazole

HRID 2102001
Notes
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Reaction equation

HRID 2102001 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[C:3]=1[Cl:13].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:21][C:22]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[O:24][N:23]=1>CN(C=O)C>[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[N:6]([CH2:21][C:22]3[N:26]=[C:25]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=4)[O:24][N:23]=3)[C:7]([CH2:9][CH3:10])=[N:8][C:4]=2[C:3]=1[Cl:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27366223-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleHCID 578001585-bromo-4-chloro-2-ethyl-1H-benzimidazole

Product 1

HCID 578002445-Bromo-4-chloro-2-ethyl-1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-benzimidazoleYield 138%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
90 °C

Procedure

5-Bromo-4-chloro-2-ethyl-1H-benzimidazole (0.100 g, 0.385 mmol), Cs2CO3 (0.188 g, 0.578 mmol), and 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.152 g, 0.578 mmol) were combined in DMF (10 mL) and heated to 90° C. for 30 min. The reaction mixture was partitioned between Et2O and water. The combined organic portions were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) provided the title compound 0.258 g: MS (ESI) m/z 487 (M+1).

Workup

  1. customThe reaction mixture was partitioned between Et2O and water
  2. washThe combined organic portions were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-9136ae1eafe946f4858318a6d609d367
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572820B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes