Water → HCID 22387787, compound

HRID 1699945Notes

Reaction equation

HRID 1699945 reaction equation
[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][C:14]=3[Cl:22])[C:9]([CH3:11])=[N:10][C:5]2=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:29](I)([CH3:31])[CH3:30].O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([O:21][CH:29]([CH3:31])[CH3:30])=[O:20])=[CH:15][C:14]=3[Cl:22])[C:9]([CH3:11])=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 22388035HCID 22388035, compound

Product 1

HCID 22387787HCID 22387787, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromo-3-(2-chloro-4-carboxybenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine (400 mg) in N,N-dimethylformamide (4 ml) were successively added potassium carbonate (218 mg) and isopropyl iodide (197 mg), and the mixture was stirred at room temperature for 24 hr. Water and ethyl acetate were added for partitioning. The organic layer was successively washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Hexane was added to the residue and the mixture was heated and allowed to cool. The precipitated crystals were collected by filtration. The crystals were dried under reduced pressure and by heating to give the objective compound (394 mg) as gray-brown crystals.

Workup

  1. customfor partitioning
  2. washThe organic layer was successively washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionHexane was added to the residue
  6. temperaturethe mixture was heated
  7. temperatureto cool
  8. filtrationThe precipitated crystals were collected by filtration
  9. customThe crystals were dried under reduced pressure
  10. temperatureby heating

Sources & evidence

ORD record
ord-f57f9d6a8a5f411f98b1d0b5be92d122
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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