Ethyl Acetate → HCID 69198828, compound

HRID 2376247Notes

Reaction equation

HRID 2376247 reaction equation
C(OCC)(=O)C.[CH3:7][O:8][C:9](=[O:42])[CH:10]=[CH:11][CH:12]([C:35]1[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=1)[CH2:13][C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[N:16]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:15]=1>[Ni].C(O)C>[CH3:7][O:8][C:9](=[O:42])[CH2:10][CH2:11][CH:12]([C:35]1[CH:36]=[C:37]([CH3:41])[CH:38]=[CH:39][CH:40]=1)[CH2:13][C:14]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=2)[N:16]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:15]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 68876041HCID 68876041, compound

Product 1

HCID 69198828HCID 69198828, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a flask containing ethyl acetate (1.0 mL), ethanol (1.0 mL) and a catalytic amount of Raney nickel was added 5-[5-(3,4-dichloro-phenyl)-1-(4-methoxy-phenyl)-1H-pyrazol-3-yl]-4-m-tolyl-pent-2-enoic acid methyl ester (92 mg, 0.17 mmol). The reaction mixture was stirred under H2 (˜1 atm) for 2 h and then filtered through a CELITE® pad. The filtrate was concentrated under reduced pressure, and the crude residue was purified by reversed-phase HPLC giving the desired ester (81 mg, 91%). HPLC: Rt=3.68 (Method B). MS (ESI): mass calculated for C29H28Cl2N3O3, 522.15; m/z found, 523.3 [M+H]+.

Workup

  1. filtrationfiltered through a CELITE® pad
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe crude residue was purified by reversed-phase

Sources & evidence

ORD record
ord-d11dd60cc21448fd80218635dc6ba1f4
Source dataset
uspto-grants-2008_12
Patent number
US07465808B2

Reaction notes

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