Cesium carbonate → 1H-Imidazole, 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-

HRID 1803153Notes

Reaction equation

HRID 1803153 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[F:7][C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[C:10]([O:17][CH3:18])[C:9]=1F.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:9]2[C:10]([O:17][CH3:18])=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[F:7])[CH:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 66859027HCID 66859027, compoundHCID 178478287HCID 178478287, compound

Product 1

HCID 668581431H-Imidazole, 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-Yield 22.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Step M (5): A mixture of 4-chloro-1H-imidazole (102 mg, 1.00 mmol), 1,2-difluoro-3-methoxy-5-nitrobenzene (200 mg, 1.00 mmol), and cesium carbonate (325 mg, 1 mmol) in acetonitrile (6 mL) was heated at 80° C. for 12 h. The reaction mixture was quenched with 1 N HCl. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (20% EtOAc/hexane) to afford 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-1H-imidazole (60 mg, 22% yield).

Workup

  1. customThe reaction mixture was quenched with 1 N HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-15fbd86ae2dc41fd9597c307c7b87f66
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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