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

HRID 2266589Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:30])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[C:10](=[O:17])[NH:11]2.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Cl[C:44](OC(=O)C)([F:46])[F:45]>[Cl-].[NH4+]>[CH3:1][O:2][C:3](=[O:31])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([CH3:30])=[C:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH2:28][CH3:29])(=[O:27])=[O:26])=[CH:21][CH:20]=1)[C:10]([O:17][CH:44]([F:46])[F:45])=[N:11]2

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of [3-(4-ethanesulfonylbenzyl)-8-fluoro-4-methyl-2-oxo-1,2-dihydroquinolin-5-yloxy]acetic acid methyl ester (0.33 g), N,N-dimethylformamide (5.0 mL), potassium carbonate (0.16 g) and acetic acid chlorodifluoromethyl ester (1.2 mL) was stirred at 70° C. for 3 days. The mixture was diluted with saturated aqueous ammonium chloride solution, extracted with ethyl acetate and the combined extracts washed with saturated aqueous sodium chloride solution and then dried over magnesium sulfate. The solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel, eluting with dichloromethane gave title as a white solid, 0.10 g.

Workup

extractionextracted with ethyl acetate
washthe combined extracts washed with saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customThe solvent was removed under reduced pressure and purification of the residue by column chromatography on silica gel
washeluting with dichloromethane
customgave title as a white solid, 0.10 g

Sources & evidence

ORD record: ord-22700ee6a8a641cd8ea4b684ba9ed337
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858640B2

Reaction notes

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