Hydrogen Peroxide → 2-(3,5-Dichloro-1-oxido-pyridine-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),5'-[1,3]dioxane]-6-yl}ethanone

HRID 2196114

Reaction equation

HRID 2196114 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:29])[C:7]=1[CH2:8][C:9]([C:11]1[C:26]2[O:25][CH2:24][C:18]3([CH2:23][O:22][CH2:21][O:20][CH2:19]3)[CH2:17][O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10].[OH:30]O>C(Cl)Cl.C[Re](=O)(=O)=O>[Cl:29][C:6]1[CH:5]=[N+:4]([O-:30])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C:9]([C:11]1[C:26]2[O:25][CH2:24][C:18]3([CH2:23][O:22][CH2:21][O:20][CH2:19]3)[CH2:17][O:16][C:15]=2[C:14]([O:27][CH3:28])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 250055272-(3,5-Dichloropyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),5'-[1,3]dioxane]-6-yl}ethanone

Product 1

HCID 250062622-(3,5-Dichloro-1-oxido-pyridine-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),5'-[1,3]dioxane]-6-yl}ethanone

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3,5-Dichloropyridin-4-yl)-1-{9-methoxy-spiro[2H-1,5-benzodioxepin-3(4H),5′-[1,3]dioxane]-6-yl}ethanone [130] (100 mg) in CH2Cl2 (2 mL) was added 30% H2O2 (120 pt) and methyltrioxorhenium(VII) (5 mg). The mixture was stirred for 18 h and subsequently washed with water. The organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure. Standard HPLC purification afforded 85 mg of the product.

Workup

  1. washsubsequently washed with water
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated to dryness under reduced pressure
  4. customStandard HPLC purification

Sources & evidence

ORD record
ord-fdcee16146a84de0911e2a0e02bb9680
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Linked notes

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