Potassium Carbonate → HCID 66810464, compound

HRID 1097533Notes

Reaction equation

HRID 1097533 reaction equation
F[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=1[NH:23][C:24](=[O:36])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:18][C:17]=1[NH:23][C:24](=[O:36])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:33])[F:34])[CH:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11217860Methyl 2-Fluoro-5-nitrobenzoateHCID 66810436N-(2-Fluoro-5-hydroxyphenyl)-3-(trifluoromethyl)benzeneacetamide

Product 1

HCID 66810464HCID 66810464, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-fluoro-5-nitrobenzoate (1.65 g, 8.29 mmol) and N-(2-fluoro-5-hydroxyphenyl)-2-[3-(trifluoromethyl)phenyl]acetamide (2.60 g, 8.30 mmol) produced in Example 53(i) in N,N-dimethylformamide (17 mL) was added potassium carbonate (1.72 g, 12.5 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was diluted with ethyl acetate (90 mL), washed successively with water (2×90 mL) and saturated brine (90 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: ethyl acetate), and the obtained solution was concentrated under reduced pressure to give the title compound (3.78 g, 93%) as a brown oil.

Workup

  1. washwashed successively with water (2×90 mL) and saturated brine (90 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: ethyl acetate)
  5. concentrationthe obtained solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e77f2103b9f6428daaaddee972bec6b2
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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