5-bromo-4-chloro-2-ethyl-1H-benzimidazole → 4-chloro-2-ethyl-1H-benzimidazole-5-carbonitrile

HRID 1188496Notes

Reaction equation

HRID 1188496 reaction equation
Br[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:14]([Cu])#[N:15]>CN1C(=O)CCC1>[Cl:13][C:3]1[C:4]2[N:8]=[C:7]([CH2:9][CH3:10])[NH:6][C:5]=2[CH:11]=[CH:12][C:2]=1[C:14]#[N:15]

Participants

4

Reactant 2

HCID 578001585-bromo-4-chloro-2-ethyl-1H-benzimidazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 674049024-chloro-2-ethyl-1H-benzimidazole-5-carbonitrileYield 35.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
220 °C

Procedure

5-Bromo-4-chloro-2-ethyl-1H-benzimidazole (0.050 g, 0.192 mmol) and CuCN (0.030 g, 0.576 mmol) were combined in NMP (3 mL) and heated to 220° C. for 20 min in a microwave. The cooled mixture was partitioned between Et2O and water. The organic portion was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification (SiO2, EtOAc/hexanes) afforded the title compound (0.014 g): MS (ESI) m/z 206 (M+1).

Workup

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

Sources & evidence

ORD record
ord-1aac6763ee2a4347961c286c4bdf7ab2
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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