Sodium Methoxide → 6-(benzylthio)-1-(5,6-dichloro-2-methoxypyridin-3-yl)quinolin-2(1H)-one

HRID 1504486Notes

Reaction equation

[CH2:1]([S:8][C:9]1[CH:10]=[CH:11][C:12]([NH:22][C:23]2[C:24]([O:31][CH3:32])=[N:25][C:26]([Cl:30])=[C:27]([Cl:29])[CH:28]=2)=[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[C:24]([O:31][CH3:32])=[N:25][C:26]([Cl:30])=[C:27]([Cl:29])[CH:28]=1)[C:17](=[O:19])[CH:16]=[CH:15]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A RBF was charged with (E)-ethyl 3-(5-(benzylthio)-2-((5,6-dichloro-2-methoxypyridin-3-yl)amino)phenyl)acrylate (2.54 g, 5.19 mmol) and MeOH (25.9 ml) to give a yellow suspension. Sodium methoxide, 0.5M solution in methanol (4.15 ml, 2.076 mmol) was added. A reflux condenser was attached, and the reaction was heated to 70° C. and stirred overnight. The reaction was cooled to RT and filtered through a pad of Celite/silica gel and then washed with MeOH and then with DCM. The reaction was concentrated, dissolved in IPA, and heated to 110° C. The solution was filtered, cooled to RT, and concentrated to afford 6-(benzylthio)-1-(5,6-dichloro-2-methoxypyridin-3-yl)quinolin-2(1H)-one (2.10 g, 4.74 mmol, 91% yield) as a light yellow solid. m/z (ESI) 443.0 (M+H)+.

Workup

customto give a yellow suspension
customA reflux condenser was attached
temperatureThe reaction was cooled to RT
filtrationfiltered through a pad of Celite/silica gel
washwashed with MeOH
concentrationThe reaction was concentrated
dissolutiondissolved in IPA
temperatureheated to 110° C
filtrationThe solution was filtered
temperaturecooled to RT
concentrationconcentrated

Sources & evidence

ORD record: ord-7a182e6744ac44f7aeecd87256e7e664
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212182B2

Reaction notes

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