HCID 9849876, compound → HCID 21262826, compound

HRID 567951Notes

Reaction equation

HRID 567951 reaction equation
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([O:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-])=O)=[CH:31][CH:30]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]>CCO.[Pd]>[F:38][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([O:28][C:29]3[CH:30]=[CH:31][C:32]([NH2:35])=[CH:33][CH:34]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]

Participants

4

Reactant 1

HCID 9849876HCID 9849876, compound

Product 1

HCID 21262826HCID 21262826, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-{2-[3,4-bis(difluoromethoxy)phenyl]-2-[6-(4-nitrophenoxy)-3-pyridyl]ethyl}pyridine (600 mg, 1.13 mmol) from Example 6, Step 5 in 20 mL EtOH, was added 120 mg of Pd/C 10% and the resulting mixture was stirred 20 h under H2 atmosphere. The reaction was filtered on celite, washed with ethyl acetate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (10% EtOH/Ethyl acetate) to afford the amine as an oil (500 mg, 88%).

Workup

  1. filtrationThe reaction was filtered on celite
  2. washwashed with ethyl acetate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel (10% EtOH/Ethyl acetate)

Sources & evidence

ORD record
ord-923202b6828440f5a0c0d9935d413fb2
Source dataset
uspto-grants-2001_01
Patent number
US06180650B2

Reaction notes

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