Sodium Methoxide → HCID 117736910, compound

HRID 1504539Notes

Reaction equation

HRID 1504539 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][CH:23]2[CH2:27][CH2:26][CH:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)[CH2:24]2)=[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]([CH:23]1[CH2:27][CH2:26][CH:25]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([F:34])[CH:29]=3)[CH2:24]1)[C:17](=[O:18])[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 Methoxide2×HCID 117749009HCID 117749009, compound

Product 1

HCID 117736910HCID 117736910, compoundYield 23.53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
100 °C

Procedure

A 25-mL pressure vessel was charged with (E)-ethyl 3-(5-(benzylthio)-2-((3-(3-fluorophenyl)cyclopentyl)amino)phenyl)acrylate (800 mg, 1.682 mmol), methanol (8.4 ml), and a solution of sodium methoxide in methanol (0.5 M, 3.4 mL, 1.682 mmol). The reaction. vessel was sealed with a Teflon cap and the yellow reaction mixture was warmed to 100° C. After 36 h, additional solution of sodium methoxide in methanol (0.5 M, 3.4 mL, 1.682 mmol) was added and the reaction vessel was sealed and warmed to 100° C. After 12 h, the reaction mixture was allowed to cool to ambient temperature and concentrated under reduced pressure to furnish a yellow residue, which was purified by flash column chromatography (50-g Biotage column, eluent: gradient, 20 to 30% EtOAc in heptane) to afford 6-(benzylthio)-1-(3-(3-fluorophenyl)cyclopentyl)quinolin-2(1H)-one (170 mg, 0.396 mmol, 23.53% yield). m/z (ESI) 430.1 (M+H)+.

Workup

  1. customThe reaction
  2. customcap
  3. customthe reaction vessel was sealed
  4. temperaturewarmed to 100° C
  5. waitAfter 12 h
  6. temperatureto cool to ambient temperature
  7. concentrationconcentrated under reduced pressure
  8. customto furnish a yellow residue, which
  9. customwas purified by flash column chromatography (50-g Biotage column, eluent: gradient, 20 to 30% EtOAc in heptane)

Sources & evidence

ORD record
ord-893604e2c87a439f819359778c5c9b2c
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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