関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 1,10-Phenanthroline | HCID 1318 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 2-Bromoaniline | HCID 11992 | — |
| 反応物 | 5-Bromo-pyridine-2-carbonyl chloride | HCID 19090771 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 2-(5-Bromo-2-pyridinyl)benzoxazole | HCID 46941613 | 30% |
反応手順
A mixture of 2-bromoaniline (3.90 g, 22.7 mmol), 5-bromopyridine-2-carbonyl chloride (5.00 g, 22.7 mmol), Cs2CO3 (14.78 g, 45.36 mmol), 1,10-phenanthroline (0.409 g, 2.27 mmol), CuI (0.216 g, 1.13 mmol) and anhydrous 1,4-dioxane (40 mL) was degassed with argon for about 40 min while stirring. The stirring reaction mixture was then maintained under argon at about 120° C. for about 40 h. Upon completion, the reaction was cooled to RT and poured over CH2Cl2 (300 mL). The organics were then washed with sat. NaHCO3, H2O and brine, dried over MgSO4, filter and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO2, 4:1 dichloromethane-hexanes) and subsequent recrystallization from hexanes afforded compound 11 (1.86 g, 30% yield) as colorless fibers.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09328086B2 |
|---|
| 出典データセット | uspto-grants-2016_05 |
|---|
| ORD ID | ord-3c0af32c96b544d6aa712ca19029fe13 |
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| 出典メモ | uspto-grants-2016_05 |
|---|
