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

HRID 1188497Notes

Reaction equation

HRID 1188497 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH3:12])[NH:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:13]#[N:14].C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:22][C:23]1[N:27]=[C:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[CH:29]=2)[O:25][N:24]=1>CN(C=O)C>[Cl:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH3:12])[N:7]([CH2:22][C:23]3[N:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[C:30]([C:34]([F:37])([F:35])[F:36])[CH:29]=4)[O:25][N:24]=3)[C:6]=2[CH:5]=[CH:4][C:3]=1[C:13]#[N:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27366223-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleHCID 674049024-chloro-2-ethyl-1H-benzimidazole-5-carbonitrile

Product 1

HCID 674070874-Chloro-2-ethyl-1-({5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-1H-benzimidazole-5-carbonitrileYield 12.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloro-2-ethyl-1H-benzimidazole-5-carbonitrile (0.014 g, 0.068 mmol), Cs2CO3 (0.033 g, 0.102 mmol), and 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.027 g, 0.102 mmol) were combined in DMF (10 mL) and heated to 90° C. for 30 min. The cooled reaction mixture was partitioned between Et2O and water. The organic portion was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.0037 g): MS (ESI) m/z 432 (M+1).

Workup

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

Sources & evidence

ORD record
ord-aaf527ee139d48e988ab758e34fa53ac
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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