Cesium carbonate → Methyl 4-fluoro-2-(6-nitropyridin-3-yloxy)benzoate

HRID 573121Notes

Reaction equation

HRID 573121 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19](Cl)=[CH:18][N:17]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][C:19]2[CH:18]=[N:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2598065-Chloro-2-nitropyridineHCID 2775386Methyl 4-fluorosalicylate

Product 1

HCID 67226297Methyl 4-fluoro-2-(6-nitropyridin-3-yloxy)benzoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-fluoro-2-hydroxybenzoate (23.5 g) and 2-nitro-5-chloropyridine (21.9 g) in N,N-dimethylformamide (120 mL) was added cesium carbonate (45 g). The mixture was stirred at 50° C. overnight. The mixture was diluted with ethyl acetate (800 mL) and washed three times with water and brine. After drying over Na2SO4 and filtration, the solvent was evaporated under vacuum and the residue was purified by silica gel chromatography (2% ethyl acetate in dichloromethane) to give the title compound.

Workup

  1. washwashed three times with water and brine
  2. dry with materialAfter drying over Na2SO4 and filtration
  3. customthe solvent was evaporated under vacuum
  4. customthe residue was purified by silica gel chromatography (2% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-ef8daf91281f4f5f9267b0639ee577e9
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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