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

HRID 2095772Notes

Reaction equation

HRID 2095772 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][N:10]=1>CO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:7]2[CH:6]=[CH:5][C:4]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[CH:3][C:2]=2[F:1])=[N:10][CH:11]=1

Participants

4

Reactant 1

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

Product 1

HCID 58158488Tert-butyl {4-[(5-aminopyridin-2-yl)oxy]-3-fluorophenyl}carbamateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of tert-butyl {3-fluoro-4-[(5-nitropyridin-2-yl)oxy]phenyl}carbamate (15 g, 42.9 mmol) in methanol (300 mL) was added 5 wt % palladium/carbon (3.0 g), and the mixture was stirred at room temperature for 8 hr under a hydrogen atmosphere. After nitrogen substitution, insoluble material was collected by filtration and washed with methanol. The solvent of the filtrate was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure to give the title compound (12.3 g, 90%).

Workup

  1. filtrationAfter nitrogen substitution, insoluble material was collected by filtration
  2. washwashed with methanol
  3. customThe solvent of the filtrate was evaporated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-dd13b4f1c11746f785b37c6129310d92
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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