反応 #1563640
ord-7b9c899c70254f1dba9e6bafb41a413e
反応方程式
反応物
反応条件
後処理
- 1その他was degassed with argon gas for 30 min
- 2ろ過Then the reaction mixture was filtered through Celite bed
- 3洗浄the Celite bed was washed with ice cold water (2×100 mL)
- 4抽出The filtrate was extracted with EtOAc (20 mL)
- 5乾燥dried over anhydrous sodium sulphate
- 6ろ過filtered
- 7濃縮concentrated
- 8その他to afford 150 mg of crude product
- 9その他The crude product was purified by silica gel chromatography over (eluent: 5% MeOH/DCM)
実験手順
A stirred solution of 6-bromo-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indazole-4-carboxamide, 3 (200 mg, 0.464 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)piperazine (154 mg, 0.510 mmol) and Na2CO3 (123 mg, 1.160 mmol) in a mixture of water (3 mL) and DMF (15 mL) was degassed with argon gas for 30 min. Then PdCl2(PPh3)2 (16.28 mg, 0.023 mmol) was added and heated to 120° C. for 3 h. Then the reaction mixture was filtered through Celite bed and the Celite bed was washed with ice cold water (2×100 mL). The filtrate was extracted with EtOAc (20 mL), dried over anhydrous sodium sulphate, filtered, and concentrated to afford 150 mg of crude product. The crude product was purified by silica gel chromatography over (eluent: 5% MeOH/DCM) to afford the title compound as an off-white solid (85 mg, 32%). 1H NMR (DMSO-d6, 400 MHz): δ 0.889 (t, J=14.4 Hz, 3H), 1.554-1.483 (m, 8H), 2.134 (s, 3H), 2.55 (s, 3H), 4.411 (d, J=1.6 Hz, 2H), 5.059 (m, 1H), 5.913 (s, 1H), 7.830 (s, 1H), 8.047 (s, 1H), 8.08 (s, 1H), 8.306 (s, 1H), 8.462 (s, 1H), 11.53 (s, 1H), 13 (brs, 1H). LCMS (ES+) m/z=528.2.