Ethyl Acetate → HCID 86700039, compound

HRID 1428089Notes

Reaction equation

HRID 1428089 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[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>[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:18](=[O:28])[C:19]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:20][N:21]([CH2:3][C:4]3[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=3)[CH:22]=2)=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 127522194-(Bromomethyl)pyridine hbrHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 86700039HCID 86700039, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-(Bromomethyl)pyridine hydrobromide (290 mg) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (200 mg) and cesium carbonate (998 mg) in DMF (5 ml) at room temperature. The reaction mixture was stirred at 100° C. overnight. 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 [chloroform:methanol=10:0->19:1->9:1 (v/v)], and the eluate was concentrated under reduced pressure. The residue was purified by PLC [dichloromethane:methanol=10:1 (v/v)] to give 126 mg 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 [chloroform:methanol=10:0->19:1->9:1 (v/v)]
  8. concentrationthe eluate was concentrated under reduced pressure
  9. customThe residue was purified by PLC [dichloromethane:methanol=10:1 (v/v)]

Sources & evidence

ORD record
ord-374a365b1d1840ce8a878c3e215d4194
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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