Calcium Carbonate → HCID 11737199, compound

HRID 1071843Notes

Reaction equation

HRID 1071843 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2[N:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[Ca+2]>C(O)C.[Pd]>[F:18][C:14]1[CH:13]=[C:12]([C:7]2[CH:6]=[C:5]([N:19]([CH3:21])[CH3:20])[C:4]3[C:9](=[CH:10][CH:11]=[CH:2][CH:3]=3)[N:8]=2)[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 11371372HCID 11371372, compound

Product 1

HCID 11737199HCID 11737199, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[6-bromo-2-(3-fluorophenyl)-4-quinolinyl]-N,N-dimethylamine (2.5 g, 7.55 mmoles) and 300 mg of a catalyst consisting of 5% palladium on a calcium carbonate support in 200 mL of ethanol was placed under a hydrogen atmosphere at 50 psi and shaken for 48 hrs. At the end of this time the atmosphere was replaced by nitrogen and the mixture concentrated. Solids containing insoluble quinoline hydrobromide salts were washed with ethyl acetate and 5% sodium hydroxide solution and residual solids removed by filtration. Filtrates were combined, the layers were separated, and the organic layer was recovered, dried over Na2SO4, filtered and concentrated. The extracted material was recrystallized from methylene chloride and hexane to provide 700 mg (37%) of the title compound.

Workup

  1. concentrationthe mixture concentrated
  2. additionSolids containing insoluble quinoline hydrobromide salts
  3. washwere washed with ethyl acetate and 5% sodium hydroxide solution and residual solids
  4. customremoved by filtration
  5. customthe layers were separated
  6. customthe organic layer was recovered
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe extracted material was recrystallized from methylene chloride and hexane

Sources & evidence

ORD record
ord-143d01a245bb45828b810784f7cdaf0c
Source dataset
uspto-grants-2005_06
Patent number
US06906193B2

Reaction notes

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