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Benzoyl chloride → 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Benzoyl chloride | HCID 7412 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 5-Bromo-N,N-Dimethyltryptamine | HCID 360252 | — |
| 触媒 | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | Ammonia | HCID 222 | 3% |
| 生成物 | 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole | HCID 19600443 | 167.3% |
反応手順
Benzoyl chloride (1.7 mL, 14.6 mmol) was added to a solution of 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (Example 3a, 9.5 mmol) in dichloromethane (70 mL) containing triethylamine (4 mL, 28.7 mmol) and DMAP (206 mg, 1.7 mmol). The resulting solution was stirred at room temperature for 20 h. Dilution with dichloromethane (500 mL) was followed by sequential washing with water (200 mL) and brine (150 mL), drying over sodium sulfate and removal of the solvent in vacuo. Flash chromatography (silica gel, 3-5% 2M methanolic ammonia in dichloromethane) yielded 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1-benzoylindole (2.95 g, 84%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05998438 |
| 出典データセット | uspto-grants-1999_12 |
| ORD ID | ord-7797e7fb49944762b4a1c1951ca1d748 |
| 出典メモ | uspto-grants-1999_12 |