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Ethyl Acetate → Ethyl 1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

HRID 1428084
Notes
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Reaction equation

HRID 1428084 reaction equation
CC1C=CC(S(O[CH2:12][CH2:13][F:14])(=O)=O)=CC=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23](=[O:33])[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][NH:26][CH:27]=2)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C=O)C>[F:14][CH2:13][CH2:12][N:26]1[CH:27]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][CH:20]=2)[C:23](=[O:33])[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 86700035Ethyl 1-(2-fluoroethyl)-5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylateYield 29.8%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluoroethyl 4-methylbenzenesulfonate (1.00 g) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (1.00 g) and cesium carbonate (2.49 g) in DMF (9 ml) at room temperature. The reaction mixture was stirred at 80° C. for two hours. The reaction mixture was returned to room temperature and diluted by adding ethyl acetate. The organic layer was washed with water and brine and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, the residue was purified by silica gel column chromatography [ethyl acetate:hexane:methanol=1:1:0->7:3:0->1:0:0->19:0:1 (v/v)] to give 0.35 g of the title compound as an oily substance.

Workup

  1. customwas returned to room temperature
  2. additiondiluted
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [ethyl acetate:hexane:methanol=1:1:0->7:3:0->1:0:0->19:0:1 (v/v)]

Sources & evidence

ORD record
ord-9bc181e7c7004466a32dcb752ea23d18
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933103B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes