Potassium Carbonate → HCID 68785003, compound

HRID 2266490Notes

Reaction equation

HRID 2266490 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:26])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)[C:10](=[O:17])[NH:11]2.C(=O)([O-])[O-].[K+].[K+].Cl[C:35](OC(=O)C)([F:37])[F:36]>O>[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:26])=[C:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=1)[C:10]([O:17][CH:35]([F:37])[F:36])=[N:11]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68608867HCID 68608867, compoundHCID 86613376Chlorodifluoromethyl acetate

Product 1

HCID 68785003HCID 68785003, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [3-(4-chlorobenzyl)-8-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]acetic acid methyl ester (1.0 g), N7N-dimethylformamide (15 mL), potassium carbonate (0.89 g) and acetic acid chlorodifluoromethyl ester (1.1 mL) was stirred at 70° C. for 18 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined extracts dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with a mixture of pentane and dichloromethane (4:1 by volume) gave title compound as a white solid, 0.49 g.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined extracts dried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
  4. washeluting with a mixture of pentane and dichloromethane (4:1 by volume)

Sources & evidence

ORD record
ord-21f02fb816e843bc816e365e6f1bad68
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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