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

HRID 1800489Notes

Reaction equation

HRID 1800489 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:32])[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[CH:22]=2)=[CH:15][C:14]=1[OH:33])#[N:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:30]([C:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[C:20]([NH:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]#[N:12])=[C:14]([O:33][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:15]=1)=[O:32])([CH3:29])[CH3:28])#[N:31]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 68416945N-(4-cyano-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 684179083-(1-cyano-1-methylethyl)-N-{4-cyano-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamideYield 24.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-5-nitropyridine (1.06 g, 6.68 mmol) and N-(4-cyano-3-hydroxyphenyl)-3-(1-cyano-1-methylethyl)benzamide (2.0 g, 6.55 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (1.35 g, 9.82 mmol), and the mixture was stirred at 80° C. for 20 hr. The reaction mixture was cooled to room temperature, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with water (150 mL) and saturated brine (150 mL×2), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→40/60), and further purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100). The obtained solution was concentrated under reduced pressure to give the title compound (0.68 g, 24%) as a pale-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. additionThe obtained residue was diluted with ethyl acetate (300 mL)
  5. washwashed with water (150 mL) and saturated brine (150 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe insoluble material was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→40/60)
  10. customfurther purified by basic silica gel column chromatography (hexane/ethyl acetate=70/30→0/100)
  11. concentrationThe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f657c39f51f84cd8baeb78892eb4b30e
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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