Potassium Carbonate → HCID 117737264, compound

HRID 1504381Notes

Reaction equation

HRID 1504381 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12](F)=[C:13]([C:15](=[O:30])/[CH:16]=[C:17](/[NH:19][C:20]2[CH:25]=[C:24]([F:26])[C:23]([Br:27])=[CH:22][C:21]=2[O:28][CH3:29])\[CH3:18])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][CH:10]=1)[N:19]([C:20]1[CH:25]=[C:24]([F:26])[C:23]([Br:27])=[CH:22][C:21]=1[O:28][CH3:29])[C:17]([CH3:18])=[CH:16][C:15]2=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 117737207HCID 117737207, compound

Product 1

HCID 117737264HCID 117737264, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (E)-1-(5-(benzylthio)-2-fluorophenyl)-3-((4-bromo-5-fluoro-2-methoxyphenyl)amino)but-2-en-1-one (3.7 g, 7.34 mmol) in dimethyl sulfoxide (20 mL) was added potassium carbonate (2.028 g, 14.67 mmol), and the reaction was stirred at 80° C. After 2 hours, the reaction mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic layer was concentrated and purified by column chromatography, eluting with 20-60% (3:1 ethanol/ethyl acetate) in heptane, to provide 6-(benzylthio)-1-(4-bromo-5-fluoro-2-methoxyphenyl)-2-methylquinolin-4(1H)-one (2.2 g, 4.54 mmol, 61.9% yield) as an off-white solid. LC/MS (ESI+): m/z (ESI) 484.0, 486.0 (M+H; two bromine isotopes).

Workup

  1. temperaturethe reaction mixture was cooled to ambient temperature
  2. custompartitioned between water and ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. custompurified by column chromatography
  5. washeluting with 20-60% (3:1 ethanol/ethyl acetate) in heptane

Sources & evidence

ORD record
ord-cb1e4bd7da554410a4fbb01ce13d825d
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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