Hydrochloric Acid → HCID 86700038, compound

HRID 1428088Notes

Reaction equation

HRID 1428088 reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N: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]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:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:18](=[O:28])[C:19]([C:23]([OH:25])=[O:24])=[CH:20][N:21]([CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=3)[CH:22]=2)=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 66771917Ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate

Product 1

HCID 86700038HCID 86700038, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(Bromomethyl)pyridine hydrobromide (126 mg) was added to a suspension of ethyl 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylate (100 mg) and cesium carbonate (437 mg) in DMF (2 ml) at room temperature. The reaction mixture was stirred at room temperature overnight. The reaction mixture was stirred at 80° C. for four hours and returned to room temperature. A 1 N aqueous sodium hydroxide solution (2 ml) was added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature for 1.5 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 94 mg of the title compound as a solid.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for four hours
  2. customreturned to room temperature
  3. stirringThe reaction mixture was stirred at room temperature for 1.5 hours
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-5d7b9f5b87f344bc94e1b465fde4c9aa
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

Loading…