Cesium carbonate → HCID 66810574, compound

HRID 1097512Notes

Reaction equation

HRID 1097512 reaction equation
[Cl:1][C:2]1[C:18]([C:19]([C:22]#[N:23])([CH3:21])[CH3:20])=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:8]=1[F:14])=[O:5].F[C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[N+:32]([O-:34])=[O:33].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[NH2:29][C:28]1[CH:30]=[CH:31][C:25]([O:13][C:11]2[CH:10]=[CH:9][C:8]([F:14])=[C:7]([NH:6][C:4](=[O:5])[C:3]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([C:22]#[N:23])([CH3:21])[CH3:20])[C:2]=3[Cl:1])[CH:12]=2)=[C:26]([N+:32]([O-:34])=[O:33])[CH:27]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 677684-Fluoro-3-nitroanilineHCID 66810467HCID 66810467, compound

Product 1

HCID 66810574HCID 66810574, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-3-(1-cyano-1-methylethyl)-N-(2-fluoro-5-hydroxyphenyl)benzamide (2.0 g, 6.01 mmol) and 4-fluoro-3-nitroaniline (940 mg, 6.02 mmol) in N,N-dimethylformamide (12 mL) was added cesium carbonate (2.94 g, 9.02 mmol), and the mixture was stirred at 80° C. for 16 hr. The reaction mixture was cooled to room temperature, insoluble material was filtered off and washed with ethyl acetate. The filtrate and washings were combined and the mixture was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (120 mL), and washed with saturated aqueous sodium hydrogen carbonate solution (120 mL). The aqueous layer was extracted with ethyl acetate (120 mL). The combined organic layer was washed with saturated brine (120 mL×2), and dried over anhydrous sodium sulfate. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80→100/0), and the obtained solution was concentrated under reduced pressure to give the title compound (1.66 g, 59%) as a yellow powder.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationinsoluble material was filtered off
  3. washwashed with ethyl acetate
  4. concentrationthe mixture was concentrated under reduced pressure
  5. additionThe obtained residue was diluted with ethyl acetate (120 mL)
  6. washwashed with saturated aqueous sodium hydrogen carbonate solution (120 mL)
  7. extractionThe aqueous layer was extracted with ethyl acetate (120 mL)
  8. washThe combined organic layer was washed with saturated brine (120 mL×2)
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationInsoluble material was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure
  12. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=20/80→100/0)
  13. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-36af39be8f704519b7cf08028d7faf56
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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