Water → Benzyl 2-methoxy-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylate

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Reaction Conditions

Reaction Steps

Sodium carbonate (2.0 M in water; 4.0 mL, 8.09 mmol) was added to a solution of benzyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (1.26 g, 3.45 mmol) and (2-methoxypyridin-3-yl)boronic acid (0.58 g, 3.79 mmol) in N,N-dimethylformamide (12 mL). Dichloro [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.25 g, 0.345 mmol) was added and the mixture was heated to 70° C. After 2 h, the mixture was cooled to ambient temperature and water was added. The mixture was extracted with ethyl acetate and the combined organic extracts were dried over magnesium sulfate and concentrated. Purification by silica gel chromatography (100% hexanes→50% hexanes/ethyl acetate) to give the title compound (0.815 g). MS 325.2 (M+1).

Provenance & Evidence