反应详情

温度

100 °C

A stirred mixture of 1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-ol (22.00 g, 86.18 mmol) cesium carbonate (28.08 g, 86.18 mmol), 1,2-difluoro-4-nitrobenzene (13.71 g, 86.18 mmol) and DMA (100 mL) was heated to 100° C. for 1 hour. After cooling to room temperature, the mixture was partitioned between DCM (500 mL) and water (500 mL). The phases were separated, and the organic phase washed with water (3×200 mL), dried (Na2SO4), filtered, and concentrated in vacuo. The resulting residue was triturated with diethyl ether (100 mL) and hexanes (200 mL) co-solvent, and the resulting beige powder was filtered. A second crop was obtained after cooling in a −10° C. freezer overnight. The two crops were combined (28 g, 82%). 1H NMR (400 MHz, CDCl3) δ 8.45 (d, J=5.5 Hz, 1H), 8.16 (m, 2H), 7.86 (s, 1H), 7.39 (m, 1H), 7.35 (d, J=8.6 Hz, 2H), 6.84 (d, J=8.2 Hz, 2H), 6.48 (d, J=5.5 Hz, 1H), 5.65 (s, 2H), 3.76 (s, 3H). 19F NMR (376 MHz, CDCl3) δ −124.2 (m).

1. temperatureAfter cooling to room temperature
2. customthe mixture was partitioned between DCM (500 mL) and water (500 mL)
3. customThe phases were separated
4. washthe organic phase washed with water (3×200 mL)
5. dry with materialdried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe resulting residue was triturated with diethyl ether (100 mL) and hexanes (200 mL) co-solvent
9. filtrationthe resulting beige powder was filtered
10. customA second crop was obtained
11. temperatureafter cooling in a −10° C. freezer overnight