Hydrochloric Acid → 6-(benzylthio)-1-(4-bromo-5-fluoro-2-methoxyphenyl)quinolin-2(1H)-one

HRID 1504402Notes

Reaction equation

[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][C:23]2[CH:28]=[C:27]([F: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+].Cl>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]([F: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

Conditions

Temperature: 100 °C

Procedure

(E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-fluoro-2-methoxyphenyl)amino)phenyl)-acrylate (0.400 g, 0.775 mmol was added to a flask followed by MeOH (10.00 mL) and sodium methoxide (1.6 mL, 1.641 mmol). The flask was fitted with reflux condensor and heated to 100° C. for 1 hour. The reaction was cooled to RT and poured into 20 mL HCl (IN). Extracted with EtOAc (3×), dried over magnesium sulfate and filtered. The resulting material was concentrated and used without further purification to yield 0.362 g of 6-(benzylthio)-1-(4-bromo-5-fluoro-2-methoxyphenyl)quinolin-2(1H)-one. m/z (ESI) 516.0 (M+H)+.

Workup

customThe flask was fitted
temperaturewith reflux condensor
temperatureThe reaction was cooled to RT
extractionExtracted with EtOAc (3×)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationThe resulting material was concentrated
customused without further purification

Sources & evidence

ORD record: ord-a1cbb8a26c8a4e3fa42b12426d73ffdc
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

Loading…