反应详情

温度

0 °C

To a cooled (−78° C.) solution of di-tert-butyl{4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-7-yl}imidodicarbonate (1 g, 2 mmol) in anhydrous THF (10 mL) was added lithium diisopropylamide (2 M in THF, 1.47 mL, 2.94 mmol), and the mixture stirred for 30 min. Boric acid, trimethyl ester (0.371 mL, 3.26 mmol) was added, and the mixture stirred for 10 min before warming to 0° C. The mixture was quenched with water (0.2 mL) and warmed to RT. The THF was removed by rotary evaporation, and the residue was partitioned between ethyl acetate and water. Following separation of the layers, the organic layer was dried over sodium sulfate and evaporated. To the resulting foam was added heptane, and the solution was stirred until the particles were reduced to a powdery solid. The mixture was filtered and washed with heptane (10×). The solid was dried under vacuum to afford 0.6 g (60%) of the title compound as a beige solid. 1H NMR (400 MHz, CD3OD): δ 8.23 (s, 1 H), 8.22 (s, 1 H), 8.01 (s, 1 H), 7.07 (s, 1 H), 4.39-4.18 (m, 1 H), 3.93-3.70 (m, 1 H), 2.26-2.13 (m, 2 H), 2.11-1.92 (m, 4 H), 1.60-1.53 (m, 2 H), 1.33 (s, 18 H), 0.93 (s, 9 H), 0.12 (s, 6 H).

1. stirringthe mixture stirred for 10 min
2. customThe mixture was quenched with water (0.2 mL)
3. temperaturewarmed to RT
4. customThe THF was removed by rotary evaporation
5. customthe residue was partitioned between ethyl acetate and water
6. customseparation of the layers
7. dry with materialthe organic layer was dried over sodium sulfate
8. customevaporated
9. additionTo the resulting foam was added heptane
10. stirringthe solution was stirred until the particles
11. filtrationThe mixture was filtered
12. washwashed with heptane (10×)
13. customThe solid was dried under vacuum