Ethanol → tert-butyl 6-(6-cyclopropylpyridin-3-yl)-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate

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Reaction Steps

tert-Butyl 6-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate (0.34 g, 0.90 mmol), 2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.20 g, 0.82 mmol), PdCl2×dppf (0.050 g), saturated sodium carbonate (2 mL), EtOH (4 mL) and toluene (4 mL) were stirred at 80° C. for 2 h. The solution was cooled to RT, taken up in water (15 mL) and extracted three times with EtOAc-Et2O. The combined organic phases were dried, filtered and concentrated. Purification by column chromatography with EtOAc-heptanes (1:1 through 3:1) and EtOAc-MeOH (9:1) as eluents gave 0.22 g (70%) of tert-butyl 6-(6-cyclopropylpyridin-3-yl)-3,4-dihydro-2,7-naphthyridine-2(1H)-carboxylate as a white solid.

Provenance & Evidence