HCID 69259880, compound → HCID 69259873, compound

HRID 584033Notes

Reaction equation

HRID 584033 reaction equation
[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([C:23](=[O:31])[C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[CH:17]=2)=[C:10]([CH3:32])[CH:9]=1)=[O:6]>CCO.CCOC(C)=O.[Ni]>[CH3:1][O:2][C:3](=[O:33])[CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH3:32])[C:11]([O:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH:23]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[OH:31])[CH:17]=2)=[C:12]([CH3:14])[CH:13]=1)=[O:6]

Participants

4

Reactant 1

HCID 69259880HCID 69259880, compound

Product 1

HCID 69259873HCID 69259873, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of N-{4-[3-(4-fluoro-benzoyl)-4-hydroxy-phenoxy]-3,5-dimethyl-phenyl}-malonamic acid methyl ester (222 mg, 0.49 mmol) in a mixture of EtOH/EtOAc (4:1, 25 mL) was added nickel catalyst (2 mL, water and methanol washed). The mixture was hydrogenated under 50 psi at room temperature for 1 h. The catalyst was filtered off and the filtrate was concentrated. The residue was purified by preparative TLC to give the title compound of Step A (159 mg) as a white solid. MS (APCl−) Calc.: 453.2. Found: 452.2 (M−1).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-c007be799f3949caa21e76907d2eb0b5
Source dataset
uspto-grants-2005_08
Patent number
US06924310B2

Reaction notes

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