HCID 22612101, compound → HCID 22612153, compound

HRID 844035Notes

Reaction equation

HRID 844035 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[N:25]=[CH:24][CH:23]=[CH:22][C:8]=2[C:9]([NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[O:10])=[CH:4][CH:3]=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][NH:11][C:9](=[O:10])[C:8]2[CH:22]=[CH:23][CH:24]=[N:25][C:7]=2[O:6][C:5]2[CH:26]=[CH:27][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 22612101HCID 22612101, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22612153HCID 22612153, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a degassed solution of 2-(4-Fluoro-phenoxy)-N-(4-nitro-benzyl)-nicotinamide (0.800 g 2.17 mmole) in ethyl acetate was added 10% palladium on carbon (0.160 g). This was shaken under 40 psi hydrogen for 30 minutes. The catalyst was removed by filtration, and the solution was concentrated to give an oil that was purified by chromatography on silica gel eluting with 4% methanol/methylene chloride. Recrystalization from ethyl acetate/hexane gave a solid. (0.562 g). 1H NMR (400 mhz, CDCl3) d 3.64 (s, 2H), 4.58 (d, J=5.60 Hz, 2H), 6.64 (d, J=8.30 Hz, 2H), 7.05 (m, 7H), 8.02 (s, broad , 1H), 8.20 (m, 1H), 8.62 (d, 1H).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution was concentrated
  3. customto give an oil that
  4. customwas purified by chromatography on silica gel eluting with 4% methanol/methylene chloride
  5. customRecrystalization from ethyl acetate/hexane
  6. customgave a solid

Sources & evidence

ORD record
ord-e9a961082c414dfbac4ab48de4bbee38
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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