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Potassium Carbonate → [4-difluoromethoxy-2-ethyl-8-fluoro-3-(4-fluorobenzyl)quinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266550
Notes
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Reaction equation

HRID 2266550 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8](=[O:27])[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)=[C:10]([CH2:17][CH3:18])[NH:11]2.C(=O)([O-])[O-].[K+].[K+].Cl[C:36](OC(=O)C)([F:38])[F:37]>O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:27][CH:36]([F:38])[F:37])=[C:9]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:10]([CH2:17][CH3:18])=[N:11]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68783191[2-ethyl-8-fluoro-3-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic Acid Methyl EsterHCID 86613376Chlorodifluoromethyl acetate

Product 1

HCID 68780260[4-difluoromethoxy-2-ethyl-8-fluoro-3-(4-fluorobenzyl)quinolin-5-yloxy]acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
70 °C

Procedure

A mixture of [2-ethyl-8-fluoro-3-(4-fluorobenzyl)-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (1.5 g), N/N-dimethylformamide (30 mL), potassium carbonate (5.2 g) and acetic acid chlorodifluoromethyl ester (5.5 mL) was stirred at 70° C. for 4 days. The mixture was diluted with water and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (3:1 by volume) to afford title compounds, 0.50 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. customthe solvent removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with a mixture of cyclohexane and ethyl acetate (3:1 by volume)
  6. customto afford title compounds, 0.50 g

Sources & evidence

ORD record
ord-6abe094a6f414a35971c3b9a2fb659ce
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07858640B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes