反应详情

温度

65 °C

A stirred mixture of 1-(4-methoxybenzyl)-4-(2-fluoro-4-nitrophenoxy)-3-iodo-1H-pyrazolo[3,4-b]pyridine (10.4 g, 20.0 mmol), stannous chloride-dihydrate (22.6 g, 100.0 mmol), and absolute EtOH (200 mL) was heated to 65° C. for 1.5 hours under N2. After cooling to room temperature, the reaction was concentrated in vacuo, and then diluted with DCM (100 mL) and water (100 mL). Aqueous 2N NaOH was added until the pH of the aqueous phase was in the 11-12 range. The biphasic suspension was filtered through a pad of celite, rinsing with DCM (3×100 mL). The filtered biphase was separated, and the aqueous phase was re-extracted with DCM (3×75 mL). The combined organic phases were dried (Na2SO4), filtered, and concentrated. Yield: 7.90 g, 78%. The product was used in the next step without purification. 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=6 Hz, 1H), 7.35 (d, J=9 Hz, 2H), 7.03 (t, J=9 Hz, 1H), 6.83 (d, J=9 Hz, 2H), 6.53 (m, 2H), 6.24 (m, 1H), 5.61 (s, 2H), 3.81 (s, 2H), 3.76 (s, 3H).

1. temperatureAfter cooling to room temperature
2. concentrationthe reaction was concentrated in vacuo
3. additiondiluted with DCM (100 mL) and water (100 mL)
4. additionAqueous 2N NaOH was added until the pH of the aqueous phase
5. filtrationThe biphasic suspension was filtered through a pad of celite
6. washrinsing with DCM (3×100 mL)
7. customThe filtered biphase was separated
8. extractionthe aqueous phase was re-extracted with DCM (3×75 mL)
9. dry with materialThe combined organic phases were dried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customThe product was used in the next step without purification