Hydrochloric Acid → HCID 86700032, compound

HRID 1428082Notes

Reaction equation

HRID 1428082 reaction equation
Br[CH2:2][CH2:3][O:4][CH3:5].[F:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:14](=[O:24])[C:15]([C:19]([O:21]CC)=[O:20])=[CH:16][NH:17][CH:18]=2)=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+].Cl>CN(C=O)C.O>[F:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[C:14](=[O:24])[C:15]([C:19]([OH:21])=[O:20])=[CH:16][N:17]([CH2:2][CH2:3][O:4][CH3:5])[CH:18]=2)=[CH:11][CH:12]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonate2×HCID 14798Sodium HydroxideHCID 809722-Bromoethyl methyl ether2×HCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 86700032HCID 86700032, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Bromo-2-methoxyethane (95 μl) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (200 mg) and cesium carbonate (499 mg) in DMF (4 ml) at room temperature. The reaction mixture was stirred at room temperature for four hours. Then the reaction mixture was stirred at 50° C. overnight. Cesium carbonate (499 mg) and 1-bromo-2-methoxyethane (95 μl) were added to the reaction mixture at 50° C. The reaction mixture was stirred at 50° C. for nine hours. Then the reaction mixture was stirred at 80° C. for three days and returned to room temperature. A 1 N aqueous sodium hydroxide solution (4 ml) was added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature for five hours. A 1 N aqueous hydrochloric acid solution and water were added to the reaction mixture. The precipitated solid was collected by filtration, washed with water and then washed with a mixed solvent of hexane and diethyl ether [5:1 (v/v)] to give 113 mg of the title compound as a solid.

Workup

  1. stirringThen the reaction mixture was stirred at 50° C. overnight
  2. stirringThe reaction mixture was stirred at 50° C. for nine hours
  3. stirringThen the reaction mixture was stirred at 80° C. for three days
  4. customreturned to room temperature
  5. stirringThe reaction mixture was stirred at room temperature for five hours
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with water
  8. washwashed with a mixed solvent of hexane and diethyl ether [5:1 (v/v)]

Sources & evidence

ORD record
ord-b79dc6fe482b401c988c5b86b8a841cd
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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