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

Participants

Reaction Conditions

Reaction Steps

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)+.

Provenance & Evidence