Potassium Carbonate → Benzyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

HRID 56868

Reaction equation

HRID 56868 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]2[C:21]([O:22][CH3:23])=[CH:20][NH:19][C:18](=[O:24])[CH:17]=2)[CH:9]=1.Br[CH2:26][C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28].[Cl-].[Li+]>CN(C)C=O.O>[Cl:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]2[C:21]([O:22][CH3:23])=[CH:20][N:19]([CH2:26][C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[C:18](=[O:24])[CH:17]=2)[CH:9]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 433294Lithium ChlorideHCID 1176049354-Chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile

Product 1

HCID 117622981Benzyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3.18 g (23.0 mmol) of potassium carbonate were added to a solution of 4.00 g (15.3 mmol) of 4-chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile and 2.92 ml (18.4 mmol) of benzyl bromoacetate in 53.3 ml of dimethylformamide, and the mixture was then stirred at 100° C. for 45 min. The reaction mixture was cooled to RT and the reaction was ended by adding 530 ml of water and 10.0 g (236 mmol) of lithium chloride. The mixture was extracted three times with 200 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was dissolved in 50 ml of dichloromethane, applied to diatomaceous earth and purified by flash chromatography (120 g cartridge, 80 ml/min, ethyl acetate/cyclohexane gradient). Yield: 3.90 g (61% of theory)

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionThe mixture was extracted three times with 200 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in 50 ml of dichloromethane
  7. custompurified by flash chromatography (120 g cartridge, 80 ml/min, ethyl acetate/cyclohexane gradient)

Sources & evidence

ORD record
ord-ee94b06db5ee4be4aeede6faed6236f7
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Linked notes

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