Dimethylformamide → [8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

HRID 2266508Notes

Reaction equation

HRID 2266508 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8](=[O:30])[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][C:20]=1[Cl:29])=[C:10]([CH3:17])[NH:11]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:44](OC(=O)C)([F:46])[F:45]>O>[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]2[C:7]=1[C:8]([O:30][CH:44]([F:46])[F:45])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][C:20]=1[Cl:29])[C:10]([CH3:17])=[N:11]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 68780451HCID 68780451, compoundHCID 86613376Chlorodifluoromethyl acetate

Product 1

HCID 68784446[8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-4-difluoromethoxy-2-methylquinolin-5-yloxy]acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [8-chloro-3-(2-chloro-4-methanesulfonylbenzyl)-2-methyl-4-oxo-1,4-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.34 g), N,N-dimethylformamide (15 mL), potassium carbonate (0.58 g) and acetic acid chlorodifluoromethyl ester (0.4 mL) was stirred at 70° C. for 16 hours. The mixture was diluted with water, extracted with ethyl acetate and the combined extracts were dried over sodium sulfate and then the solvent removed under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (7:3 by volume) gave title compound, 0.37 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. customPurification of the residue by column chromatography on silica gel
  5. washeluting with a mixture of cyclohexane and ethyl acetate (7:3 by volume)

Sources & evidence

ORD record
ord-35dd80803ab44f03b90152995a133a21
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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