HCID 12071522, compound → HCID 12071524, compound

HRID 1369066Notes

Reaction equation

HRID 1369066 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]#[C:12][CH2:13][CH2:14][OH:15])[CH:8]=[C:7]2[C:3]=1[C:4]([OH:34])([C:24]1[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=1)[C:5](=[O:23])[N:6]2[CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20]>CO.[Pd]>[Cl:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:8]=[C:7]2[C:3]=1[C:4]([OH:34])([C:24]1[CH:33]=[CH:32][C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=1)[C:5](=[O:23])[N:6]2[CH2:16][CH2:17][N:18]([CH2:21][CH3:22])[CH2:19][CH3:20]

Participants

4

Reactant 1

HCID 12071522HCID 12071522, compound

Product 1

HCID 12071524HCID 12071524, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Under nitrogen stream, to a solution of 4-chloro-6-(4-hydroxy-1-butynyl)-1-(2-diethylaminoethyl)-3-hydroxy-3-(2-naphthyl)oxindole (8.6 mg, 0.0180 mmol) in methanol (1.5 mL) was added 10% palladium/carbon (4.0 mg). The mixture was stirred under hydrogen atmosphere at room temperature for one hour. After filtration with Celite, the solvent was removed to give the title compound (8.7 mg).

Workup

  1. filtrationAfter filtration with Celite
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-cfe4110951c04c6cb2beff6683821529
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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