反応 #674295
ord-a37fc8f051724aec9244c9a4b3868890
反応方程式
反応物
溶媒
反応条件
後処理
- 1その他It was degassed again
- 2workup.ADDITIONrefilled with N2 (2 times)
- 3温度(heating bath) for 16 hrs
- 4温度The reaction mixture was cooled to room temperature
- 5workup.ADDITIONH2O (30 mL) was added
- 6抽出The aqueous phase was extracted with EtOAc (30 mL) and DCM (3×30 mL)
- 7乾燥The combined organic phase was dried over anhydrous Na2SO4
- 8濃縮concentrated by evaporation in vacuo
- 9その他to give black residue which
- 10その他was purified by CombiFlash (40 g silica gel column, Hexane/EtOAc)
実験手順
tert-Butyl 6-(4-bromo-1H-pyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate (145 mg, 0.42 mmol) and (±)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (268 mg, 0.63 mmol) were added to a round bottom flask. It was vacuumed and refilled with N2 (3 times). DME (2.0 mL) and a solution of Na2CO3 (2.0 M, 1.0 mL) were sequentially added. It was vacuumed and refilled with N2 (3 times). Pd(PPh3)2Cl2 (14.7 mg, 0.021 mmol) was added. It was degassed again refilled with N2 (2 times). The mixture was stirred at 90° C. (heating bath) for 16 hrs. The reaction mixture was cooled to room temperature and H2O (30 mL) was added. The aqueous phase was extracted with EtOAc (30 mL) and DCM (3×30 mL). The combined organic phase was dried over anhydrous Na2SO4, concentrated by evaporation in vacuo to give black residue which was purified by CombiFlash (40 g silica gel column, Hexane/EtOAc) to afford (±)-tert-butyl 6-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)-2-azaspiro[3.3]heptane-2-carboxylate (106 mg, 45%) as a off-white solid.