Ethyl Acetate → HCID 86700041, compound

HRID 1428091Notes

Reaction equation

HRID 1428091 reaction equation
Br[CH2:2][C:3]([O:5]C(C)(C)C)=[O:4].[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18](=[O:28])[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][NH:21][CH:22]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[CH2:26]([O:25][C:23]([C:19]1[C:18](=[O:28])[C:17]([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=2)=[CH:22][N:21]([CH2:2][C:3]([OH:5])=[O:4])[CH:20]=1)=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 86700041HCID 86700041, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl bromoacetate (341 μl) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (400 mg) and cesium carbonate (998 mg) in DMF (8 ml) at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted by adding ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and filtered, and the filtrate was then concentrated under reduced pressure. Dichloromethane (15 ml) and TFA (0.59 ml) were added to the residue at room temperature. The reaction mixture was stirred at room temperature for two hours. TFA (1.00 ml) was added to the reaction mixture at room temperature. The reaction mixture was stirred overnight. TFA (4.00 ml) was added to the reaction mixture at room temperature. The reaction mixture was stirred overnight. Water was added to the reaction mixture, and the organic layer was extracted with ethyl acetate, washed with brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=19:1->17:3 (v/v)] to give 320 mg of the title compound as a solid.

Workup

  1. additionThe reaction mixture was diluted
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was then concentrated under reduced pressure
  6. additionDichloromethane (15 ml) and TFA (0.59 ml) were added to the residue at room temperature
  7. stirringThe reaction mixture was stirred at room temperature for two hours
  8. additionTFA (1.00 ml) was added to the reaction mixture at room temperature
  9. stirringThe reaction mixture was stirred overnight
  10. additionTFA (4.00 ml) was added to the reaction mixture at room temperature
  11. stirringThe reaction mixture was stirred overnight
  12. additionWater was added to the reaction mixture
  13. extractionthe organic layer was extracted with ethyl acetate
  14. washwashed with brine
  15. dry with materialdried over sodium sulfate
  16. filtrationAfter filtration
  17. concentrationthe filtrate was concentrated under reduced pressure
  18. customthe residue was purified by silica gel column chromatography [chloroform:methanol=19:1->17:3 (v/v)]

Sources & evidence

ORD record
ord-a772e369b4144dc5a9efcaab5eea2e72
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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