Triacetoxyperiodinane → 1-(5-(4-Bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-methoxy-2-(4-morpholinophenyl)ethanone

HRID 56583Notes

Reaction equation

HRID 56583 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2[O:14][N:13]=[C:12]([CH:15]([OH:31])[CH:16]([O:29][CH3:30])[C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[N:11]=2)=[CH:4][C:3]=1[O:32][CH3:33].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.CCOCC.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:1][C:2]1[C:3]([O:32][CH3:33])=[CH:4][C:5]([C:10]2[O:14][N:13]=[C:12]([C:15](=[O:31])[CH:16]([O:29][CH3:30])[C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[N:11]=2)=[CH:6][C:7]=1[O:8][CH3:9]

Participants

7

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58431986HCID 58431986, compound

Product 1

HCID 584321201-(5-(4-Bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-methoxy-2-(4-morpholinophenyl)ethanoneYield 70%

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 24477Sodium ThiosulfateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1-(5-(4-bromo-3,5-dimethoxyphenyl)-1,2,4-oxadiazol-3-yl)-2-methoxy-2-(4-morpholinophenyl)ethanol (0.18 g, 0.35 mmol) in anhydr CH2Cl2 (4 mL) under argon was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (0.198 g, 0.47 mmol). After stirring at room temperature for 50 min, the mixture was diluted with Et2O, saturated aqueous NaHCO3 and 20% Na2S2O3. The layers were separated and the organic layer was washed with saturated NaHCO3, dried over Na2SO4 and concentrated in vacuo. Purification by chromatography (40-50% EtOAc-hexanes) gave the product as a bright yellow solid (0.1249 g, 70% yield). MS: m/z 518.1 [M+H]+.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography (40-50% EtOAc-hexanes)

Sources & evidence

ORD record
ord-83394170892d4ca280786a319977f271
Source dataset
uspto-grants-2016_09
Patent number
US09434707B2

Reaction notes

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