4-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide → 4-hydroxy-3-methoxy-N-[3-(2-phenylethyl)phenyl]-phenylacetamide

HRID 7068

Reaction equation

HRID 7068 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:26][CH3:27]>C(OCC)(=O)C.[Pd]>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:26][CH3:27]

Participants

4

Reactant 1

HCID 220196124-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide2×

Product 1

HCID 220196454-hydroxy-3-methoxy-N-[3-(2-phenylethyl)phenyl]-phenylacetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]phenylacetamide (the compound of Example 36) (250 mg) is dissolved in ethyl acetate (10 ml), and thereto is added 10% palladium on carbon (25 mg), and the mixture is subjected to catalytic hydrogenation at 25° C. The catalyst is removed by filtration, and the solvent is evaporated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (200 mg).

Workup

  1. customis subjected to catalytic hydrogenation at 25° C
  2. customThe catalyst is removed by filtration
  3. customthe solvent is evaporated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-618c50e72df147e99a9b64fa3649d28f
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Linked notes

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