Water → 3-Ethoxycarbonyl-5,8-difluoro-4-(3-trifluoromethylphenylmercapto)quinoline

HRID 266074

Reaction equation

HRID 266074 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:13])[CH:8]=[CH:9][C:10]=2[F:12])[N:5]=[CH:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].[F:19][C:20]([F:29])([F:28])[C:21]1[CH:22]=[C:23]([SH:27])[CH:24]=[CH:25][CH:26]=1.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[CH2:17]([O:16][C:14]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[S:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:19])([F:28])[F:29])[CH:22]=1)=[C:10]([F:12])[CH:9]=[CH:8][C:7]=2[F:13])=[O:15])[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 1367513-(Trifluoromethyl)benzenethiolHCID 17040076Ethyl 4-chloro-5,8-difluoroquinoline-3-carboxylate

Product 1

HCID 28010183-Ethoxycarbonyl-5,8-difluoro-4-(3-trifluoromethylphenylmercapto)quinolineYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction mixture of 100.0 mg (0.37 mmol) of 4-chloro-3-ethoxycarbonyl-5,8-difluoroquinoline, 80.3 mg (0.44 mmol) of 3-trifluoromethylthiophenol and 80 μL of diisopropylethylamine in 2.0 mL of N,N-dimethylformamide was stirred at room temperature for 2 h and cooled. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulphate and concentrated. The resulting residue was purified on silica gel column eluting with ethyl acetate-hexane (1:3) to give 30.0 mg (20%) of the title compound.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe resulting residue was purified on silica gel column
  7. washeluting with ethyl acetate-hexane (1:3)

Sources & evidence

ORD record
ord-f9cd45ab8dd54a679adfeff65ba01e40
Source dataset
uspto-grants-1997_07
Patent number
US05650415

Linked notes

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