HCID 13394284, compound → HCID 13394287, compound

HRID 2164301Notes

Reaction equation

HRID 2164301 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](=[O:19])[C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]=1)[NH:7][C:6](=[O:20])[CH:5]2SC>O1CCCC1.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11](=[O:19])[C:12]3[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=3)[CH:10]=1)[NH:7][C:6](=[O:20])[CH2:5]2

Participants

4

Reactant 1

HCID 13394284HCID 13394284, compound

Product 1

HCID 13394287HCID 13394287, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 30.5 g (0.091 mol) of 5-chloro-7-(4-fluorobenzoyl)-3-methylthioindolin-2-one in 2.5 l of tetrahydrofuran was stirred vigorously and treated with 285 g of wet Raney nickel for 6 minutes. The mixture was filtered and the filter cake obtained was washed with 200 ml of tetrahydrofuran. The resulting filtrate was evaporated to leave 20.2 g of residue. This residue was recrystallized from acetone to give 16.8 g (64%) of the titled compound as white, fluffy needles, mp. 222°-225° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filter cake obtained
  3. washwas washed with 200 ml of tetrahydrofuran
  4. customThe resulting filtrate was evaporated

Sources & evidence

ORD record
ord-8b8b64e8d392423986777d8cdf644a43
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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