Hydrochloric Acid → 4-(1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine

関与物質

反応手順

To a stirred solution of 1-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine (0.560 g, 1.42 mmol) in a MeOH (20 mL) and THF (5 mL) co-solvent was added zinc (0.464 g, 7.10 mmol), followed by saturated aqueous NH4Cl (5 mL). Next 6N aqueous HCl (3-4 mL) was added until all solids dissolved and the pH was 1-2. The reaction was stirred at room temperature for 18 hours. The resulting mixture was partitioned between DCM (30 mL) and saturated aqueous NH4Cl (30 mL). The phases were separated, and the aqueous phase was re-extracted with DCM (20 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated in vacuo. The resulting waxy solid (504 mg, 72%) was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=5.5 Hz, 1H), 7.72 (s, 1H), 7.32 (d, J=8.6 Hz, 2H), 7.02 (m, 1H), 6.82 (d, J=9.0 Hz, 2H), 6.40-6.55 (m, 3H), 5.61 (s, 2H), 3.82 (br s, 2H), 3.75 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −129.0 (m).

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