Ethyl Acetate → HCID 57815183, compound

HRID 385607Notes

Reaction equation

HRID 385607 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[NH:9]2)=[N:4][C:3]=1[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:21][CH:22]([O:25][CH3:26])[O:23][CH3:24].C(OCC)(=O)C>CN(C)C=O>[CH3:24][O:23][CH:22]([O:25][CH3:26])[CH2:21][N:9]1[C:10]2[C:5](=[N:4][C:3]([CH3:13])=[C:2]([F:1])[CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 816722-Bromo-1,1-dimethoxyethaneHCID 57815374HCID 57815374, compound

Product 1

HCID 57815183HCID 57815183, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 0.74 g of 7-fluoro-6-methyl-1,5-naphthyridin-2(1H)-one in 5 mL of N,N-dimethylformamide, 2.0 g of cesium carbonate and 0.84 g of 2-bromo-1,1-dimethoxyethane were added, the temperature was increased to 90 to 100° C., and the mixture was stirred for 2 hours 30 minutes. The reaction mixture was cooled to room temperature, thereto was added ethyl acetate, the insoluble substance was filtered off, and the solvent was then distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=100:1 to obtain 0.69 g of 1-(2,2-dimethoxyethyl)-7-fluoro-6-methyl-1,5-naphthyridin-2(1H)-one as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble substance was filtered off
  3. distillationthe solvent was then distilled off under reduced pressure
  4. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3415067d4478482fb2fa95072f4a50a6
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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