Pyridine → N-(6-bromo-1H-benzimidazol-2-yl)acetamide

HRID 1162465Notes

Reaction equation

HRID 1162465 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH2:10])[NH:7][C:6]=2[CH:11]=1.N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH:10][C:18](=[O:20])[CH3:19])[NH:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 204308615-Bromo-1H-1,3-benzodiazol-2-amine

Product 1

HCID 11054189N-(6-bromo-1H-benzimidazol-2-yl)acetamideYield 28%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a 250 mL round-bottomed flask was added 6-bromo-1H-benzo[d]imidazol-2-amine (2.00 g, 9.43 mmol, Carbocore, The Woodlands, Tex.), DCM (100 mL), pyridine (1.0 mL, 12.3 mmol) and acetic anhydride (0.979 mL, 10.4 mmol). The mixture was stirred at 25° C. for 18 h. The solution was concentrated and then diluted with 10% MeOH (2M in NH3)/CH2Cl2 until homogeneous and then the solution was concentrated onto silica. Purification by silica gel chromatography (0.5 to 5.0% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound as a white solid (0.676 g, 28%). MS (ESI, positive ion) m/z: 254 (M(79Br)+1).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with 10% MeOH (2M in NH3)/CH2Cl2 until homogeneous and then the solution
  3. concentrationwas concentrated onto silica
  4. customPurification by silica gel chromatography (0.5 to 5.0% MeOH (2 M in NH3)/CH2Cl2)

Sources & evidence

ORD record
ord-a1c288058d56440d9fbf8b6f44e53b9b
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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