Sodium Methoxide → HCID 117737520, compound

HRID 1504466Notes

Reaction equation

HRID 1504466 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][C:23]2[CH:28]=[C:27]([CH3:29])[C:26]([Br:30])=[CH:25][C:24]=2[O:31][CH3:32])=[C:13](/[CH:15]=[CH:16]/[C:17](OCC)=[O:18])[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][CH:10]=1)[N:22]([C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([Br:30])=[CH:25][C:24]=1[O:31][CH3:32])[C:17](=[O:18])[CH:16]=[CH:15]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 117746866HCID 117746866, compound

Product 1

HCID 117737520HCID 117737520, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A RBF was charged with (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-2-methoxy-5-methylphenyl)amino)phenyl)acrylate (5.12 g, 9.99 mmol) and MeOH (50.0 ml) to give a yellow suspension. Sodium methoxide (25 wt % in MeOH) (0.432 ml, 1.998 mmol) was added. A reflux condenser was attached, and the flask was lowered into a 70° C. heating bath. After 1 h, additional portions of MeOH (25 mL) and sodium methoxide solution (ca. 0.85 mL) were added in sequence. After 7 h, the mixture was cooled and concentrated under vacuum. The residue was purified by chromatography on silica gel (80-g Redi-Sep column, 25-g silica gel loading column, loaded as a solution in MeOH-DCM, then eluted with 25-75% EtOAc/Heptane containing 10% DCM). The fractions containing product were combined and concentrated to give 6-(benzylthio)-1-(4-bromo-2-methoxy-5-methylphenyl)quinolin-2(1H)-one (4.233 g, 9.08 mmol, 91% yield) as a tan solid. m/z (ESI) 466.1 (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. waitAfter 7 h
  6. temperaturethe mixture was cooled
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by chromatography on silica gel (80-g Redi-Sep column, 25-g silica gel loading column
  9. washeluted with 25-75% EtOAc/Heptane containing 10% DCM)
  10. additionThe fractions containing product
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-cc225effffb44292b5eb6e5a11eb0444
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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