Ammonium Chloride → 4-(4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-4-ol

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Reaction Steps

To a 0° C. solution of 5-bromo-2-(trifluoromethyl)pyridine (0.604 g, 2.68 mmol) in THF (10 mL) was added isopropyl magnesium bromide (1 mL, 2.68 mmol) in a drop-wise fashion. The reaction mixture was stirred in a cooling bath for 1 h and was then treated with 2H-pyrano[3,2-b]pyridin-4(3H)-one (200 mg, 1.34 mmol) in THF (5 mL). After stirring for 1 h, saturated NH4Cl (50 mL) was added to the reaction mixture, and the aqueous solution was extracted with EtOAc (3×10 mL). The combined organic layers were dried over Na2SO4, and concentrated. The residue was purified by column chromatography to give the desired alcohol.

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