反応 #59724
ord-ada3c6ed74304513bd5f7a6122521efc
反応方程式
反応物
反応条件
後処理
- 1その他The reaction was evaporated to dryness in vacuo
- 2その他the product was flushed through a 10 g silica SPE cartridge
- 3洗浄eluting with 95:5 ethyl acetate
- 4その他methanol, to remove inorganic material
- 5その他Without further purification the crude product
- 6workup.DISSOLUTIONwas dissolved in 1,2 dimethoxyethane (4 ml)
- 7温度The reaction was heated under nitrogen at 80° C. for 18 hours
- 8その他Solvent was removed in vacuo
- 9その他the residue was purified by mass-directed HPLC
実験手順
2-Chloromethyl-5-(4-iodophenyl)-[1,3,4]oxadiazole (Intermediate 7) (48 mg, 0.15 mmol), serinol (206 mg, 2.25 mmol) and potassium iodide (25 mg, 0.15 mmol) were dissolved in dimethylformamide (1 ml) and stirred for 18 hours at 20° C. The reaction was evaporated to dryness in vacuo and the product was flushed through a 10 g silica SPE cartridge, eluting with 95:5 ethyl acetate:methanol, to remove inorganic material. Without further purification the crude product was dissolved in 1,2 dimethoxyethane (4 ml). Tetrakis(triphenylphosphine)palladium(0) (16 mg, 0.014 mmol), N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide (Intermediate 17) (0.15 mmol) and 1M aqueous sodium carbonate (0.15 ml, 0.15 mmol) were added. The reaction was heated under nitrogen at 80° C. for 18 hours. Solvent was removed in vacuo and the residue was purified by mass-directed HPLC to yield the desired product.