Sodium Carbonate → 4-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one

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Reaction Conditions

Reaction Steps

To Na2CO3 (151 mg, 1.41 mmol) was added water (1.5 ml) and acetonitrile (2 ml) and the solution was degassed for 5 min with argon. 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]pyridine (84 mg, 0.31 mmol), 6-bromo-4-(ethoxyamino)-1H-1,5-naphthyridin-2-one (80 mg, 0.28 mmol) and Pd(dppf)Cl2 (10 mg, 0.014 mmol) were added sequentially followed by addition of acetonitrile (2 ml). The mixture was stirred at 100° C. for 15 h then allowed to cool to ambient temperature. Water and ethyl acetate were added then the phases were separated. The aqueous phase was extracted with ethyl acetate, the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo. Purification by chromatography afforded of 4-(ethoxyamino)-6-[1-(3-pyridyl)pyrazol-4-yl]-1H-1,5-naphthyridin-2-one.

Provenance & Evidence