化工社化工社 化学情報印刷レポート · 研究参考用
1,2-Dimethoxyethane → 4-(6-Chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 6-Chloro-4-methylpyridine-3-boronic acid | HCID 44119169 | — |
| 反応物 | 4-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one | HCID 68569002 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Hydrochloric Acid | HCID 313 | — |
| 生成物 | 4-(6-Chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one | HCID 72332459 | 64.9% |
反応条件
| 温度 | 130 °C |
|---|
反応手順
A microwave vial is charged with 4-iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (184 mg, 0.6 mmol), 6-chloro-4-methylpyridine-3-boronic acid (103 mg, 0.6 mmol) and bis(triphenylphosphine)palladium dichloride (21 mg, 0.03 mmol). DME (1 ml) is added, followed by 2N aqueous sodium carbonate solution (0.6 ml, 1.2 mmol) and the reaction is heated to 130° C. by microwave irradiation, with stirring, for 30 minutes. The reaction is then diluted with 2N HCl (20 ml), extracted with ethyl acetate (20 ml), and the organic layer is removed and purified by flash chromatography on silica gel to give 4-(6-chloro-4-methyl-pyridin-3-yl)-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (119 mg).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08530667B2 |
| 出典データセット | uspto-grants-2013_09 |
| ORD ID | ord-7aaa8d583ecf4c4fbab7dc484af1bd7e |
| 出典メモ | uspto-grants-2013_09 |