Potassium Iodide → HCID 59392369, compound

HRID 1512067Notes

Reaction equation

HRID 1512067 reaction equation
Br[CH2:2][CH:3]([F:5])[F:4].[Cl:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=1[C:15]1[C:24](=[O:25])[NH:23][C:18]2=[N:19][CH:20]=[CH:21][N:22]=[C:17]2[C:16]=1[O:26]C(=O)C(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.O.C(OCC)(=O)C>[Cl:6][C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([F:14])[C:8]=1[C:15]1[C:24](=[O:25])[N:23]([CH2:2][CH:3]([F:5])[F:4])[C:18]2=[N:19][CH:20]=[CH:21][N:22]=[C:17]2[C:16]=1[OH:26]

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 1361862-Bromo-1,1-difluoroethaneHCID 579988432,2-Dimethyl-propionic acid 7-(2-chloro-3,6-difluoro-phenyl)-6-oxo-5,6-dihydro-pyrido[2,3-b]pyrazin-8-yl ester

Product 1

HCID 59392369HCID 59392369, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

1-Bromo-2,2-difluoroethane (0.754 g) was added to a mixture of 2,2-dimethyl-propionic acid 7-(2-chloro-3,6-difluoro-phenyl)-6-oxo-5,6-dihydro-pyrido[2,3-1)]pyrazin-8-yl ester (Example 1.3) (1.00 g), potassium carbonate (1.76 g) and potassium iodide (catalytic amount) in anhydrous N,N-dimethylformamide (15 ml). The reaction mixture was heated in a microwave for 20 minutes at 120° C. The reaction mixture was allowed to cool to ambient temperature before diluting with water and ethyl acetate. The phases were separated. The organic phase was washed with water, dried over magnesium sulfate, and concentrated. The residue was dissolved in diethyl ether, and the solution was washed with water. The phases were separated and the organic phase was concentrated to give Compound No. B2 of Table B as an orange viscous oil (0.553 g).

Workup

  1. temperatureto cool to ambient temperature
  2. customThe phases were separated
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in diethyl ether
  7. washthe solution was washed with water
  8. customThe phases were separated
  9. concentrationthe organic phase was concentrated
  10. customto give Compound No

Sources & evidence

ORD record
ord-b2b731cf7fab41d3adca914af86b6106
Source dataset
uspto-grants-2012_07
Patent number
US08217055B2

Reaction notes

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