Sodium Methoxide → 6-(benzylthio)-1-(4-bromo-5-chloro-2-methoxyphenyl)-7-fluoroquinolin-2(1H)-one

HRID 1504424Notes

Reaction equation

HRID 1504424 reaction equation
[CH2:1]([S:8][C:9]1[C:10]([F:33])=[CH:11][C:12]([NH:22][C:23]2[CH:28]=[C:27]([Cl:29])[C:26]([Br:30])=[CH:25][C:24]=2[O:31][CH3:32])=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19]CC)=O)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][C:10]=1[F:33])[N:22]([C:23]1[CH:28]=[C:27]([Cl:29])[C:26]([Br:30])=[CH:25][C:24]=1[O:31][CH3:32])[C:17](=[O:19])[CH:16]=[CH:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 117746850(E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-chloro-2-methoxyphenyl)amino)-4-fluorophenyl)acrylate

Product 1

HCID 1177372066-(benzylthio)-1-(4-bromo-5-chloro-2-methoxyphenyl)-7-fluoroquinolin-2(1H)-oneYield 74.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A RBF was charged with (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-chloro-2-methoxyphenyl)amino)-4-fluorophenyl)acrylate (1.80 g, 3.27 mmol) and MeOH (16.3 ml) to give a yellow suspension. Sodium methoxide (25 wt % in MeOH) (0.291 ml, 1.307 mmol) was added. A reflux condenser was attached, and the flask was lowered into a 70° C. heating bath. After 16 h, the mixture was cooled and concentrated under vacuum. The residue was triturated with 2-PrOH and filtered to give 6-(benzylthio)-1-(4-bromo-5-chloro-2-methoxyphenyl)-7-fluoroquinolin-2(1H)-one (1.23 g, 2.44 mmol, 74.6% yield) as a tan solid. m/z (ESI) 504.0 (M+H)+.

Workup

  1. customto give a yellow suspension
  2. customA reflux condenser was attached
  3. customwas lowered into a 70° C.
  4. temperatureheating bath
  5. temperaturethe mixture was cooled
  6. concentrationconcentrated under vacuum
  7. customThe residue was triturated with 2-PrOH
  8. filtrationfiltered

Sources & evidence

ORD record
ord-eda0a02c6c5943adaf8f25a05485b06b
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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