Hydrogen Peroxide → 5-Chloro-4-iodo-3-(pentan-3-ylamino)picolinamide

HRID 1668847Notes

Reaction equation

HRID 1668847 reaction equation
[Cl:1][C:2]1[C:3]([I:16])=[C:4]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C(=O)([O-])[O-:18].[K+].[K+].OO>CS(C)=O.CCOC(C)=O>[Cl:1][C:2]1[C:3]([I:16])=[C:4]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[C:5]([C:8]([NH2:9])=[O:18])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 595945725-Chloro-4-iodo-3-(pentan-3-ylamino)picolinonitrile

Product 1

HCID 595945475-Chloro-4-iodo-3-(pentan-3-ylamino)picolinamideYield 85%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-4-iodo-3-(pentan-3-ylamino)picolinonitrile (55 mg, 0.16 mmol) in DMSO (1 mL) was added solid potassium carbonate (210 mg, 0.64 mmol). The mixture was cooled in an ice water bath (0° C.) and aqueous hydrogen peroxide (30%, 0.5 mL) was added. The reaction was allowed to warm to room temperature and monitored by LCMS. After the reaction was complete, the reaction mixture was diluted with EtOAc, and the organic layer was washed repeatedly with water. The organic layer was then dried over sodium sulfate, filtered and concentrated in vacuo. The residue was filtered through a silica gel plug to provide the title compound as a white solid (50 mg, 83%). The compound was characterized by LCMS (m/z=368.1 [M+H]+) and 1H NMR.

Workup

  1. additionwas added
  2. washthe organic layer was washed repeatedly with water
  3. dry with materialThe organic layer was then dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe residue was filtered through a silica gel plug

Sources & evidence

ORD record
ord-9e542c95281d489da8e6d5a5c89a00fd
Source dataset
uspto-grants-2011_08
Patent number
US07989469B2

Reaction notes

Loading…