Dimethylformamide → HCID 178428494, compound

HRID 552836Notes

Reaction equation

HRID 552836 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][NH:7][C:6]=2[C:10]=1[CH3:11].C([O-])(O)=O.[Na+].CCOC(C)=O.[CH3:23][N:24](C=O)C>>[CH3:11][C:10]1[C:6]2[NH:7][CH:8]=[N:9][C:5]=2[CH:4]=[CH:3][C:2]=1[C:23]#[N:24]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 178421694HCID 178421694, compound

Product 1

HCID 178428494HCID 178428494, compound

Conditions

Temperature
150 °C

Procedure

In a 100 ml reaction vessel, to a solution of 6-bromo-7-methyl-1H-benzimidazole (500 mg) in DMF were added Zu(CN)2 (834 mg) and Pd (PPh)4 (547 mg) at room temperature, followed by stirring at 150° C. for 5 hours. The reaction solution was poured into a 1:1 mixed solvent of a saturated NaHCO3 solution and EtOAc, followed by stirring for 1 hour. The organic layer was washed with saturated brine, dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated. It was purified by silica gel column chromatography (automatic purifier, chloroform:CH3OH=98:2 to 90:10) to obtain 7-methyl-1H-benzimidazole-6-carbonitrile (161.8 mg) as a brown solid.

Workup

  1. customIn a 100 ml reaction vessel
  2. stirringby stirring for 1 hour
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customIt was purified by silica gel column chromatography (automatic purifier, chloroform:CH3OH=98:2 to 90:10)

Sources & evidence

ORD record
ord-6f8f094310ad4e8a91535eefe8d49281
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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