Potassium Carbonate → N-{4-chloro-3-[(5-nitropyridin-2-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamide

HRID 1800512Notes

Reaction equation

HRID 1800512 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:31])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:29]#[N:30])([CH3:28])[CH3:27])[CH:21]=2)=[CH:14][C:13]=1[OH:32].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:31])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([C:29]#[N:30])([CH3:27])[CH3:28])[CH:21]=2)=[CH:14][C:13]=1[O:32][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 68418799N-(4-chloro-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 68418666N-{4-chloro-3-[(5-nitropyridin-2-yl)oxy]phenyl}-3-(1-cyano-1-methylethyl)benzamideYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (1.00 g, 6.35 mmol) and N-(4-chloro-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide (2.00 g, 6.35 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (1.31 g, 9.52 mmol), and the mixture was stirred at 70° C. for 16 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. Water (100 mL) was added to the obtained residue, and the mixture was twice extracted with ethyl acetate (50 mL)/hexane (50 mL). The combined organic layer was washed with water (150 mL) and saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography (ethyl acetate). The obtained solution was concentrated under reduced pressure to give the title compound (2.57 g, 93%) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater (100 mL) was added to the obtained residue
  5. extractionthe mixture was twice extracted with ethyl acetate (50 mL)/hexane (50 mL)
  6. washThe combined organic layer was washed with water (150 mL) and saturated brine (150 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customthe obtained residue was purified by basic silica gel column chromatography (ethyl acetate)
  11. concentrationThe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-81bdf017487a40a6af55f3e8390821d4
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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