Nitrobenzene → 2-pyridin-2-yl-5,6-bis(pyridin-3-yloxy)-1H-benzimidazole

HRID 13234Notes

Reaction equation

HRID 13234 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[N+](C1C=CC=CC=1)([O-])=O.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]2[CH:26]=[C:27]([NH2:39])[C:28]([NH2:38])=[CH:29][C:30]=2[O:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[CH:19]=1>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:39][C:27]2[CH:26]=[C:25]([O:24][C:20]3[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=3)[C:30]([O:31][C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[CH:29][C:28]=2[N:38]=1

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 142732-PyridinecarboxaldehydeHCID 231454724,5-Bis(pyridin-3-yloxy)-benzene-1,2-diamine

Product 1

HCID 231452372-pyridin-2-yl-5,6-bis(pyridin-3-yloxy)-1H-benzimidazole

Procedure

0.01 ml of pyridine-2-carboxaldehyde was added to a nitrobenzene (0.3 ml) solution of 30 mg of 4,5-bis(pyridin-3-yloxy)-benzene-1,2-diamine at 120° C., and the reaction liquid was stirred at the same temperature for 2 hours. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was evaporated away under reduced pressure, and this was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1) to obtain the entitled compound as a yellow oily substance.

Workup

  1. customthe reaction liquid
  2. customThe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  3. customThe solvent of the resulting fraction was evaporated away under reduced pressure
  4. customthis was purified
  5. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1)
  6. customto obtain the entitled compound as a yellow oily substance

Sources & evidence

ORD record
ord-1391e643d8c940e99a991612b0e29915
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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