4-Bromobenzaldehyde → 2-(4-bromophenyl)-1H-benzimidazole-4-carboxamide

HRID 736690Notes

Reaction equation

HRID 736690 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:12]([NH2:13])=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7].[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1>CO.[Pd]>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]2[NH:13][C:12]3[CH:11]=[CH:10][CH:9]=[C:5]([C:6]([NH2:8])=[O:7])[C:4]=3[N:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 707414-BromobenzaldehydeHCID 534228072,3-Diaminobenzamide dihydrochloride

Product 1

HCID 445423652-(4-bromophenyl)-1H-benzimidazole-4-carboxamideYield 17%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 2,3-diaminobenzamide dihydrochloride (synthesized as described in U.S. Pat. No. 6,737,421, column 11, EXAMPLE 2, step (e), 5 g, 22.3 mmol) and 4-bromobenzaldehyde (4.13 g, 22.3 mmol) in methanol (200 mL) was added 10% Pd/C (1.3 g). The mixture was refluxed overnight, then cooled and filtered though a pad of celite. The filtrate was concentrated under vacuum and purified by chromatography on a silica gel column with 0-10% methanol/dichloromethane to provide the title compound (1.2 g, 17%). MS (ESI) m/e 317 (M+H)+.

Workup

  1. customsynthesized
  2. temperatureThe mixture was refluxed overnight
  3. temperaturecooled
  4. filtrationfiltered though a pad of celite
  5. concentrationThe filtrate was concentrated under vacuum
  6. custompurified by chromatography on a silica gel column with 0-10% methanol/dichloromethane

Sources & evidence

ORD record
ord-7130ff23e8874b5cb93e251389332c88
Source dataset
uspto-grants-2009_09
Patent number
US07595406B2

Reaction notes

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