Potassium Carbonate → Ethyl 8-bromo-1-[6-(t-butylamino)-5-fluoropyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1274751Notes

Reaction equation

HRID 1274751 reaction equation
C(O[CH:4]=[C:5]([C:11](=[O:22])[C:12]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([Br:20])[C:13]=1F)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.BrC1C(F)=C(C=C(F)C=1F)C(CC(OCC)=O)=O.[NH2:41][C:42]1[CH:47]=[CH:46][C:45]([F:48])=[C:44]([NH:49][C:50]([CH3:53])([CH3:52])[CH3:51])[N:43]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(Cl)(Cl)Cl>[Br:20][C:14]1[C:15]([F:19])=[C:16]([F:18])[CH:17]=[C:12]2[C:13]=1[N:41]([C:42]1[CH:47]=[CH:46][C:45]([F:48])=[C:44]([NH:49][C:50]([CH3:53])([CH3:52])[CH3:51])[N:43]=1)[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]2=[O:22]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 10592111Ethyl 3-bromo-2,4,5-trifluorobenzoylacetateHCID 221212302-Amino-6-(t-butylamino)-5-fluoropyridineHCID 54232143Ethyl 2-(3-bromo-2,4,5-trifluorobenzoyl)-3-ethoxyacrylate

Product 1

HCID 22121280Ethyl 8-bromo-1-[6-(t-butylamino)-5-fluoropyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 1 ml of chloroform solution of ethyl 3-ethoxy-2-(3-bromo-2,4,5-trifluorobenzoyl)acrylate prepared from 0.65 g of ethyl 3-bromo-2,4,5-trifluorobenzoylacetate by normal process was added 0.3 g of 2-amino-6-(t-butylamino)-5-fluoropyridine. The solution was concentrated under reduced pressure to obtain yellowish orange solid residue. To this residue were added 0.4 g of anhydrous potassium carbonate and 2 ml of N,N-dimethylformamide, and the mixture was stirred at 90° C. for 25 minutes and allowed to cool. The solution was separated by adding 25 ml of chloroform and 400 ml of distilled water, and the chloroform layer was washed with 400 ml of distilled water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. After adding 2 ml of ethanol, the solution was and allowed to stand. The precipitate was dispersed in ethanol and collected by filtration, and washed with ethanol and diisopropylether successively to obtain 0.53 g of the title compound as a pale yellow powder.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customto obtain yellowish orange solid residue
  3. temperatureto cool
  4. customThe solution was separated
  5. additionby adding 25 ml of chloroform and 400 ml of distilled water
  6. washthe chloroform layer was washed with 400 ml of distilled water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionAfter adding 2 ml of ethanol
  10. additionThe precipitate was dispersed in ethanol
  11. filtrationcollected by filtration
  12. washwashed with ethanol and diisopropylether successively

Sources & evidence

ORD record
ord-e9cee47f00784b94a5131ec841f4f298
Source dataset
uspto-grants-2000_12
Patent number
US06156903

Reaction notes

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