Ethyl Acetate → HCID 57749142, compound

HRID 1874366Notes

Reaction equation

HRID 1874366 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[N:11][C:12]([N+:15]([O-])=O)=[CH:13][CH:14]=2)=[CH:4][C:3]=1[NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22].C(OCC)(=O)C>CO.[C].[Pd]>[NH2:15][C:12]1[N:11]=[CH:10][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[CH:4]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 57749141HCID 57749141, compound

Product 1

HCID 57749142HCID 57749142, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl {2-fluoro-5-[(6-nitropyridin-3-yl)oxy]phenyl}carbamate (14.2 g, 49.5 mmol) in methanol (200 mL)/ethyl acetate (200 mL) was added palladium carbon (50% water-containing product, 1.50 g), and the mixture was stirred under a hydrogen atmosphere at room temperature for 12 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, ethyl acetate) to give the title compound (9.69 g, 75%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-885b89195653467bb14fef9361077ef7
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

Loading…