Potassium tert-butoxide → 6-(benzylthio)-1-(4-bromo-5-chloro-2-methoxyphenyl)-4-methylquinolin-2(1H)-one

HRID 1504415Notes

Reaction equation

HRID 1504415 reaction equation
[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:23][C:24]2[CH:29]=[C:28]([Cl:30])[C:27]([Br:31])=[CH:26][C:25]=2[O:32][CH3:33])=[C:13](/[C:15](/[CH3:22])=[CH:16]\[C:17](OCC)=[O:18])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([S:8][C:9]1[CH:14]=[C:13]2[C:12](=[CH:11][CH:10]=1)[N:23]([C:24]1[CH:29]=[C:28]([Cl:30])[C:27]([Br:31])=[CH:26][C:25]=1[O:32][CH3:33])[C:17](=[O:18])[CH:16]=[C:15]2[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 131734327(Z)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-chloro-2-methoxyphenyl)amino)phenyl)but-2-enoate

Product 1

HCID 1177370776-(benzylthio)-1-(4-bromo-5-chloro-2-methoxyphenyl)-4-methylquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The crude residue from step 3 was dissolved in 6 mL THF, was treated with potassium tert-butoxide 1N in THF (3.05 ml, 3.05 mmol) and was heated to reflux for 20 minutes. The reaction mixture was then concentrated. The crude residue was used in the next step without purification. m/z (ESI) 502.0 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 20 minutes
  3. concentrationThe reaction mixture was then concentrated
  4. customThe crude residue was used in the next step without purification

Sources & evidence

ORD record
ord-417b2098d07449288a2fbb83a056af65
Source dataset
uspto-grants-2015_12
Patent number
US09212182B2

Reaction notes

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