Nitrobenzene → 5-(2-cyano-phenoxy)-2-pyridin-2-yl-6-(6-methanesulfonyl-pyridin-3-yloxy)-1H-benzimidazole

HRID 13294Notes

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.[C:18]([C:20]1[CH:45]=[CH:44][CH:43]=[CH:42][C:21]=1[O:22][C:23]1[CH:24]=[C:25]([NH2:41])[C:26]([NH2:40])=[CH:27][C:28]=1[O:29][C:30]1[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:34][CH:35]=1)#[N:19]>CO>[C:18]([C:20]1[CH:45]=[CH:44][CH:43]=[CH:42][C:21]=1[O:22][C:23]1[C:28]([O:29][C:30]2[CH:31]=[N:32][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:34][CH:35]=2)=[CH:27][C:26]2[NH:40][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[N:41][C:25]=2[CH:24]=1)#[N:19]

Participants

Conditions

Temperature: 120 °C

Procedure

0.007 ml of pyridine-2-carboxaldehyde and 0.5 ml of nitrobenzene were added to a methanol (1 ml) solution of 37 mg of 4-(2-cyano-phenoxy)-5-(6-methanesulfonyl-pyridin-3-yloxy)-benzene-1,2-diamine obtained in (step 5), and the reaction liquid was stirred overnight at 120° C. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1) and through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1) to obtain the entitled compound as a brown solid.

Workup

customobtained in (step 5)
customthe reaction liquid
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=20/1)
customthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=15/1)

Sources & evidence

ORD record: ord-647fd0ff4e4f4603b26ae8c5067a9f1b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Reaction notes

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