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

HRID 1848888Notes

Reaction equation

HRID 1848888 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 with water (3×) 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 with water (3×) 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-56ad45130639405b89bdad1831eb9cd3
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

Loading…