Potassium Carbonate → HCID 66810481, compound

HRID 455240Notes

Reaction equation

HRID 455240 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[F:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[NH:21][C:22](=[O:34])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:7][C:8]=1[O:20][C:17]1[CH:18]=[CH:19][C:14]([F:13])=[C:15]([NH:21][C:22](=[O:34])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)[CH:16]=1)#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5194172-Fluoro-5-nitrobenzonitrileHCID 66810436N-(2-Fluoro-5-hydroxyphenyl)-3-(trifluoromethyl)benzeneacetamide

Product 1

HCID 66810481HCID 66810481, compoundYield 94.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-cyano-4-fluoronitrobenzene (0.530 g, 3.19 mmol) and N-(2-fluoro-5-hydroxyphenyl)-2-[3-(trifluoromethyl)phenyl]acetamide (1.00 g, 3.19 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (0.530 g, 3.83 mmol), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate (100 mL), washed successively with water (100 mL) and saturated brine (100 mL), and dried over anhydrous magnesium sulfate. Insoluble material was filtered off. The obtained organic layer was purified by basic silica gel column chromatography (eluate: 50% ethyl acetate/n-hexane), and the obtained solution was concentrated under reduced pressure to give the title compound (1.38 g, 94%) as a yellow oil.

Workup

  1. washwashed successively with water (100 mL) and saturated brine (100 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationInsoluble material was filtered off
  4. customThe obtained organic layer was purified by basic silica gel column chromatography (eluate: 50% ethyl acetate/n-hexane)
  5. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8835661e8c3046b3aaffe4b515171c59
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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