Nitrobenzene → 4-(2-methoxy-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

HRID 13247Notes

Reaction equation

HRID 13247 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.[CH3:18][O:19][C:20]1[CH:41]=[CH:40][CH:39]=[CH:38][C:21]=1[O:22][C:23]1[CH:28]=[C:27]([O:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:26]=[C:25]([NH2:36])[C:24]=1[NH2:37]>>[CH3:18][O:19][C:20]1[CH:41]=[CH:40][CH:39]=[CH:38][C:21]=1[O:22][C:23]1[C:24]2[N:37]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[NH:36][C:25]=2[CH:26]=[C:27]([O:29][C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH:28]=1

Participants

4

Reactant 3

HCID 7416NitrobenzeneHCID 142732-PyridinecarboxaldehydeHCID 231457673-(2-Methoxyphenoxy)-5-(pyridin-3-yloxy)-benzene-1,2-diamine

Product 1

HCID 113388344-(2-methoxy-phenoxy)-2-pyridin-2-yl-6-(pyridin-3-yloxy)-1H-benzimidazole

Procedure

0.026 ml of pyridin-2-carboxaldehyde was added to a nitrobenzene (0.5 ml) solution of 59 mg of 3-(2-methoxyphenoxy)-5-(pyridin-3-yloxy)-benzene-1,2-diamine at 120° C., and the reaction liquid was stirred for 1 hour at the same temperature. The reaction mixture was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 to ethyl acetate to chloroform/methanol=20/1). The solvent of the resulting fraction was evaporated away under reduced pressure, and the resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1) to obtain the entitled compound as a pale yellow solid.

Workup

  1. customthe reaction liquid
  2. customThe reaction mixture was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=1/1 to ethyl acetate to chloroform/methanol=20/1)
  3. customThe solvent of the resulting fraction was evaporated away under reduced pressure
  4. customthe resulting residue was purified
  5. customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-ad6b5ca4ac614c0b8a67f8198077a98d
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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