Cesium carbonate → N-[6-(2-fluoro-4-nitrophenoxy)-3-methylimidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamide

HRID 2095841Notes

Reaction equation

HRID 2095841 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:17])=[C:9]([NH:11][C:12]([CH:14]3[CH2:16][CH2:15]3)=[O:13])[N:10]=2)[CH:7]=1.F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=1[F:28].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CS(C)=O.C(OCC)(=O)C>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH3:17])=[C:9]([NH:11][C:12]([CH:14]3[CH2:15][CH2:16]3)=[O:13])[N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 58158508N-(6-hydroxy-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 58158621N-[6-(2-fluoro-4-nitrophenoxy)-3-methylimidazo[1,2-a]pyridin-2-yl]cyclopropanecarboxamideYield 77%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(6-hydroxy-3-methylimidazo[1,2-a]pyridin-2-yl)cyclopropanecarboxamide (65 mg, 0.281 mmol) and 1,2-difluoro-4-nitrobenzene (37 μL, 0.337 mmol) in dimethyl sulfoxide (1 mL) was added cesium carbonate (137 mg, 0.422 mmol), and the mixture was stirred overnight at room temperature. Ethyl acetate and saturated aqueous ammonium chloride solution were added to the reaction mixture, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1→ethyl acetate alone) to give the title compound (80 mg, 77%) as a white solid.

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1→ethyl acetate alone)

Sources & evidence

ORD record
ord-864ece1fe8304ded8c2768990ac9f0f3
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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