Sodium Methoxide → 6-(benzylthio)-1-(5-bromo-2-methoxyphenyl)quinolin-2(1H)-one

HRID 1504437Notes

Reaction equation

[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][C:23]2[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:24]=2[O:30][CH3:31])=[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][CH:10]=1)[N:22]([C:23]1[CH:28]=[C:27]([Br:29])[CH:26]=[CH:25][C:24]=1[O:30][CH3:31])[C:17](=[O:19])[CH:16]=[CH:15]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A RBF, fitted with a reflux condenser, was charged with (E)-ethyl 3-(5-(benzylthio)-2-((5-bromo-2-methoxyphenyl)amino)phenyl)acrylate (6.92 g, 13.88 mmol) and MeOH (69.4 ml) to give a yellow suspension. Sodium methoxide (0.5N solution in methanol) (11.11 ml, 5.55 mmol) was added and the reaction was heated at 70° C. overnight. The reaction was cooled to RT and the solids were filtered over a fit and washed well with MeOH to yield 6-(benzylthio)-1-(5-bromo-2-methoxyphenyl)quinolin-2(1H)-one (5.48 g, 12.11 mmol, 87 Yo yield) as a tan solid. MS (ESI, pos. ion) m/z: [M+1] 452.0

Workup

customA RBF, fitted with a reflux condenser
customto give a yellow suspension
temperatureThe reaction was cooled to RT
filtrationthe solids were filtered over a fit
washwashed well with MeOH

Sources & evidence

ORD record: ord-df9c72fa940f48caa79cbcb4e7439f40
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

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