HCID 69259880, compound → 364332-60-5

HRID 432932Notes

Reaction equation

HRID 432932 reaction equation
C[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]>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH:23]([OH:31])[C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=2[OH:22])[O:15][C:11]2[C:12]([CH3:14])=[CH:13][C:8]([NH:7][C:5](=[O:6])[CH2:4][C:3]([OH:33])=[O:2])=[CH:9][C:10]=2[CH3:32])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 69259880HCID 69259880, compound

Product 1

HCID 9847968364332-60-5Yield 73.8%

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-aadbdbd6080c4e9e9e3eabbdeca61c92
Source dataset
uspto-grants-2003_12
Patent number
US06664291B2

Reaction notes

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