Potassium Iodide → HCID 11196679, compound

HRID 1169851Notes

Reaction equation

HRID 1169851 reaction equation
[O:1]1[C:5]2([CH2:9][CH2:8][O:7][CH2:6]2)[CH2:4][C:3]([C:10]2[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([OH:16])[CH:15]=2)=[N:2]1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[CH3:28]>CN(C)C=O.O>[CH2:27]([O:16][C:14]1[CH:15]=[C:10]([C:3]2[CH2:4][C:5]3([CH2:9][CH2:8][O:7][CH2:6]3)[O:1][N:2]=2)[CH:11]=[CH:12][C:13]=1[O:17][CH3:18])[CH3:28]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 11207411HCID 11207411, compound

Product 1

HCID 11196679HCID 11196679, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound No. 73 (1 eq) in dimethylformamide (10 mL), was added potassium iodide (0.1 eq) and potassium carbonate (2 eq). The reaction mixture was stirred at room temperature and ethyl bromide (2 eq) was added. The reaction mixture was stirred for overnight at room temperature. The reaction mixture was cooled and diluted with water, extracted with ethylacetate and washed with saturated solution of sodium chloride. The organic solvent was removed under reduced pressure. The residue thus obtained was purified by column chromatography to furnish the title compound. Yield=90%.

Workup

  1. stirringThe reaction mixture was stirred for overnight at room temperature
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted with ethylacetate
  4. washwashed with saturated solution of sodium chloride
  5. customThe organic solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b4580b1f5ebd449589a3d5b092833cdd
Source dataset
uspto-grants-2010_11
Patent number
US07825147B2

Reaction notes

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