Phenyl vinyl sulfone → 3-(Benzenesulfonyl)-2-(4-bromo-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]nonan-6-one

HRID 624298Notes

Reaction equation

HRID 624298 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4](/[CH:8]=[N:9]/[CH:10]2[CH2:14][CH2:13][N:12]([CH3:15])[C:11]2=[O:16])[CH:3]=1.[CH:17]([S:19]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[CH2:18]>C1COCC1.C([O-])(=O)C.[Ag+]>[C:22]1([S:19]([CH:17]2[CH2:18][C:10]3([CH2:14][CH2:13][N:12]([CH3:15])[C:11]3=[O:16])[NH:9][CH:8]2[C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][N:5]=2)(=[O:21])=[O:20])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 79664Phenyl vinyl sulfoneHCID 178480450HCID 178480450, compound

Product 1

HCID 896495643-(Benzenesulfonyl)-2-(4-bromo-2-pyridyl)-7-methyl-1,7-diazaspiro[4.4]nonan-6-one

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[(E)-(4-bromo-2-pyridyl)methyleneamino]-1-methyl-pyrrolidin-2-one (which may be prepared as described in Description 1) (564.3 mg, 2 mmol) and phenyl vinyl sulfone (339.8 mg, 2.02 mmol) in THF (10 mL) was treated with silver acetate (333.99 mg, 2 mmol). The mixture was stirred at room temp for 2 hours, filtered through Celite and concentrated to give the title compound (D2) as a brown gum;

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-87c462870b4e486c83cd093898bee689
Source dataset
uspto-grants-2016_04
Patent number
US09303032B2

Reaction notes

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