18-Crown-6 → HCID 178432417, compound

HRID 2102394Notes

Reaction equation

HRID 2102394 reaction equation
[Br:1][C:2]1[C:3](Cl)=[C:4]2[N:11]=[CH:10][NH:9][C:5]2=[N:6][C:7]=1[CH3:8].[F-:13].[K+].C1OCCOCCOCCOCCOCCOC1>CN1C(=O)CCC1.CCOC(C)=O.O>[Br:1][C:2]1[C:3]([F:13])=[C:4]2[N:11]=[CH:10][NH:9][C:5]2=[N:6][C:7]=1[CH3:8]

Participants

7

Reactant 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 178432416HCID 178432416, compound

Product 1

HCID 178432417HCID 178432417, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 6-bromo-7-chloro-5-methyl-3H-imidazo[4,5-b]pyridine (1.00 equivalent) in NMP is added KF (3.00 equivalents) and 18-crown-6 (0.20 equivalents) at room temperature. The resulting mixture is refluxed with stirring for 16 hours. The reaction mixture is cooled to room temperature and diluted with EtOAc and water. The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the desired product that is purified by flash column chromatography as necessary.

Workup

  1. temperatureThe resulting mixture is refluxed
  2. washThe organic layer is washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22b7b67acbac43f6ac83c7ad6a6c23d9
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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