Ethyl Acetate → 4-[1-(4-nitro-phenyl)-1H-imidazol-2-yl]-pyridine

HRID 1864726Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH:17]1[CH:21]=[CH:20][N:19]=[C:18]1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1.CCOC(C)=O>CN(C=O)C.O>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

1-Fluoro-4-nitro-benzene (80.2 g, 0.57 mmol) is dissolved in DMF (550 mL) and to that solution is added K2CO3 (157.0 g, 1.14 mmol). To that solution is added 4-(1H-imidazol-2-yl)-pyridine (55.0 g, 0.38 mmol) and the reaction is heated at 100° C. for 18 h. The solution is then cooled to RT and EtOAc (1.5 L) and water (2.0 L) are then added and the suspension is vacuum filtered. The resulting solid was then purified by column chromatography (EtOAc) to afford 4-[1-(4-nitro-phenyl)-1H-imidazol-2-yl]-pyridine as a brown solid.

Workup

temperatureThe solution is then cooled to RT
filtrationfiltered
customThe resulting solid was then purified by column chromatography (EtOAc)

Sources & evidence

ORD record: ord-53675154ffd34aa19ed46ce374f1c579
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625931B2

Reaction notes

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