1,4-Dioxane → 2-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-6,7-dihydro-5H-quinolin-8-one

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Reaction Steps

In a MW vial, 2-chloro-6,7-dihydro-5H-quinolin-8-one (0.215 g, 1.18 mmol) and tributyl-[4-methyl-2-(3-pyridyl)thiazol-5-yl]stannane (0.500 g, 1.07 mmol) were stirred in 1,4-dioxane (3.6 mL, 1.07 mmol) at ambient temperature. This yellow solution was degassed with an argon flux for 10 min and Tetrakis(PPh3)Pd(O) (0.124 g, 0.107 mmol) was added. The solution was irradiated in MW at 160° C. for 40 min. The crude was diluted with dichloromethane, NaOH (1 M) and NaHCO3 sat aq were added and aqueous layer was extracted 3 times with dichloromethane. The organic phase was then washed with brine, dried over Na2SO4 anhydrous, filtered and concentrated. Purification by column with a gradient of dichloromethane+0-10% methanol gave the title compound as a beige solid, yield: 92%. LCMS: 0.81 Min, 322 (M+1).

Provenance & Evidence