Hydrochloric Acid → HCID 86700043, compound

HRID 1428093Notes

Reaction equation

HRID 1428093 reaction equation
[O:1]=[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][NH:5][CH:4]=[C:3]1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].CC1C=CC(S(O[CH2:36][CH2:37][F:38])(=O)=O)=CC=1.Cl>CN(C=O)C>[F:38][CH2:37][CH2:36][N:5]1[CH:6]=[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2](=[O:1])[C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 2560192-Fluoroethyl p-ToluenesulfonateHCID 12624209HCID 12624209, compound

Product 1

HCID 86700043HCID 86700043, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 4-oxo-5-phenyl-1,4-dihydropyridine-3-carboxylate (190 mg) was suspended in DMF (2.5 ml). Cesium carbonate (509 mg) and 2-fluoroethyl 4-methylbenzenesulfonate (256 mg) were sequentially added and the mixture was stirred at 50° C. for three hours. A 1 N aqueous hydrochloric acid solution was added under ice cooling, and the organic layer was extracted with ethyl acetate, washed with water and brine and then dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=300:1->40:1 (v/v)] to give 181 mg of the title compound as an oily substance.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography [chloroform:methanol=300:1->40:1 (v/v)]

Sources & evidence

ORD record
ord-bfa0deae89c14ac18e5e2c2b38f4f089
Source dataset
uspto-grants-2015_01
Patent number
US08933103B2

Reaction notes

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