HCID 68536996, compound → HCID 68535251, compound

HRID 1993668Notes

Reaction equation

HRID 1993668 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][N:19]=2)[CH2:13][CH2:12]1)=[O:10]>C(O)(=O)C.[Fe]>[NH2:24][C:22]1[CH:21]=[CH:20][N:19]=[C:18]([O:17][CH:14]2[CH2:13][CH2:12][N:11]([C:9]([C:3]3[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=3[F:8])=[O:10])[CH2:16][CH2:15]2)[CH:23]=1

Participants

4

Reactant 1

HCID 68536996HCID 68536996, compound

Product 1

HCID 68535251HCID 68535251, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Add powered iron (419 mg, 7.5 mmol) to a solution of 1.1 g (3.0 mmol) of (2,6-difluoro-phenyl)-[4-(4-nitro-pyridin-2-yloxy)-piperidin-1-yl]-methanone, in glacial acetic acid (10 mL) and stir at 80° C. After 15 min, allow the mixture to reach room temperature and filter through Celite®. Wash the Celite® pad with Et2O and EtOAc. Wash the resulting organic layer with water, a saturated aqueous NaHCO3 solution and a saturated aqueous sodium chloride solution. Separate organic layer, dry over MgSO4 and evaporate solvents to afford 831 mg (83% yield) of title compound as a white solid. (ES+(m/z)=334 [M+H].

Workup

  1. customto reach room temperature
  2. filtrationfilter through Celite®
  3. washWash the Celite® pad with Et2O and EtOAc
  4. washWash the resulting organic layer with water
  5. dry with materialSeparate organic layer, dry over MgSO4
  6. customevaporate solvents

Sources & evidence

ORD record
ord-49cf3e60470b4ee4abc76d0973009114
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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