Water → Tert-butyl {3-fluoro-4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate

HRID 2095771Notes

Reaction equation

HRID 2095771 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[OH:8].Cl[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[O:8][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][N:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 783082-Chloro-5-nitropyridineHCID 11708410tert-Butyl (3-Fluoro-4-hydroxyphenyl)carbamate

Product 1

HCID 58158596Tert-butyl {3-fluoro-4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamateYield 77.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl (3-fluoro-4-hydroxyphenyl)carbamate (17.2 g, 75.7 mmol) in dimethyl sulfoxide (100 mL) were added 2-chloro-5-nitropyridine (10 g, 63.1 mmol) and cesium carbonate (30.8 g, 94.6 mmol), and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was washed with hexane/ethyl acetate (=5/1) and collected by filtration to give the title compound (17.0 g, 77%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was washed with hexane/ethyl acetate (=5/1)
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-04f8f1615d374dd68f87e28c361f21b3
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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