Sodium Bicarbonate → HCID 86715658, compound

HRID 928827Notes

Reaction equation

HRID 928827 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=1)=[C:5]2[Cl:24].C[O-].[Na+].[C:28](=O)(O)[O-:29].[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:29][CH3:28])[C:6]([CH2:13][C:14]1[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=1)=[C:5]2[Cl:24]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 86715659HCID 86715659, compound2×

Product 1

HCID 86715658HCID 86715658, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-bromo-2,4-dichloro-3-(6-(trifluoromethyl)pyridin-3-yl)methyl)quinolone (1.0 g, 2.3 mmol, Intermediate 65: step b) and sodium methoxide (1.2 g, 22 mmol) in dry toluene (12 mL) were heated to 80° C. and refluxed under a positive pressure of nitrogen overnight. The mixture was allowed to cool to ambient temperature. Aqueous saturated sodium bicarbonate solution was added to the mixture and the layers were separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to dryness. The crude material was purified by flash column chromatography (silica gel, 0-20% EtOAc-Hex) to provide the title compound as a white solid.

Workup

  1. temperaturerefluxed under a positive pressure of nitrogen overnight
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by flash column chromatography (silica gel, 0-20% EtOAc-Hex)

Sources & evidence

ORD record
ord-883f35054ab74bdba6828d29b3339230
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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