HCID 178481121, compound → HCID 9850576, compound

HRID 1369978Notes

Reaction equation

HRID 1369978 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:40])([C:33]2[N:34]([CH3:39])[C:35](S)=[N:36][CH:37]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH:13]=[C:12]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[C:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:22]=2)=[CH:4][CH:3]=1>C(O)C.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:40])([C:33]2[N:34]([CH3:39])[CH:35]=[N:36][CH:37]=2)[C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[N:15]([CH3:19])[C:14](=[O:20])[CH:13]=[C:12]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[C:28][Si:29]([CH3:30])([CH3:31])[CH3:32])[CH:22]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 178481121HCID 178481121, compound

Product 1

HCID 9850576HCID 9850576, compoundYield 81.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 702EthanolSolvent

Procedure

6-[(4-Chloro-phenyl)-hydroxy-(2-mercapto-3-methyl-3H-imidazol-4-yl)-methyl]-1-methyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one (5.0 g, 8.6 mMol) was dissolved in ethanol (40 mL) to which was added Raney™ nickel (ca. 10 g) and the reaction was heated to reflux. More RANEY™ nickel was added every 20 minutes until mass spectral analysis of the reaction showed that the starting material had been consumed. The reaction mixture was cooled to ambient temperature and filtered through CELITE™ (diatomaceous earth). The CELITE™ was washed with copious amounts of ethanol. The filtrates were combined and concentrated under vacuum to give 3.88 g of the titled compound.

Workup

  1. temperaturethe reaction was heated to reflux
  2. customhad been consumed
  3. filtrationfiltered through CELITE™ (diatomaceous earth)
  4. washThe CELITE™ was washed with copious amounts of ethanol
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8d389a5babda4743b0a66a74c2d54115
Source dataset
uspto-grants-2003_06
Patent number
US06579887B2

Reaction notes

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