Hydrochloric Acid → HCID 86700037, compound

HRID 1428087Notes

Reaction equation

HRID 1428087 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=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]CC)=[O:24])=[CH:20][NH:21][CH:22]=2)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[Na+].Cl>CN(C=O)C.O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:21]2[CH:22]=[C:17]([C:14]3[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=3)[C:18](=[O:28])[C:19]([C:23]([OH:25])=[O:24])=[CH:20]2)=[CH:4][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 86700037HCID 86700037, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-(Bromomethyl)-4-fluorobenzene (122 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 overnight. 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 two hours. A 1 N aqueous hydrochloric acid solution and water were added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water and then dried to give 250 mg of the title compound as a solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for two hours
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-704b9c7f199b4a20958a29998ad109b9
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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