化工社化工社 化学情報印刷レポート · 研究参考用
8-Hydroxyquinoline → Benzyl 4-(1-(4-(methylthio)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 8-Hydroxyquinoline | HCID 1923 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 4-Bromothioanisole | HCID 66037 | — |
| 反応物 | Benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate | HCID 67366192 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Dimethyl Sulfoxide | HCID 679 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | Benzyl 4-(1-(4-(methylthio)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate | HCID 67368480 | 95.4% |
反応条件
| 温度 | 145 °C |
|---|
反応手順
A mixture of benzyl 4-(2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (697 mg, 2.12 mmol), (4-bromophenyl)(methyl)sulfane (431 mg, 2.12 mmol, Aldrich), quinolin-8-ol (61.6 mg, 0.425 mmol, Alfa Aesar), potassium carbonate (381 mg, 2.76 mmol, EMD), Copper(I) iodide (81 mg, 0.43 mmol, Alfa Aesar) in DMSO (6 mL) was stirred at 145° C. overnight under Argon. The resulting mixture was diluted with H2O and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to a green solid. The solid was purified by flash chromatography (SiO2, 0 to 5% MeOH in CH2Cl2) to yield 911 mg of desired product as a light green solid. MS (ESI) 451 (M+H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08003796B2 |
| 出典データセット | uspto-grants-2011_08 |
| ORD ID | ord-6d9fc287bb7647da962c5755fef186ed |
| 出典メモ | uspto-grants-2011_08 |