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Indole → [2-(1H-Indol-3-ylsulfanyl)benzyl]methylamine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Indole | HCID 798 | — |
| 反応物 | Trichloroacetic Acid | HCID 6421 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | 2-Methyl-2,3-dihydro-benzo[d]isothiazole | HCID 12428808 | — |
| 反応物 | Ethyl acetate methanol triethylamine | HCID 21980445 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | [2-(1H-Indol-3-ylsulfanyl)benzyl]methylamine | HCID 15979848 | 67% |
反応手順
2-Methyl-2,3-dihydro-benzoisothiazole (VI) (Hoffmann, R. W.; Goldman, S. Chem. Ber. 111, 1978, 2716-2725) (75 mg, 0.50 mmol) was dissolved in THF (1 mL) and added to indole (V) (140 mg, 0.60 mmol) under Ar. Tricloroacetic acid (90 mg, 0.55 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. 2 mL 1N NaOH (aq) was added. Extraction with ethyl acetate (2×10 mL) and purification by flash chromatography on silica gel (eluent: ethyl acetate then ethyl acetate/methanol/triethylamine) gave 88 mg [2-(1H-Indol-3-ylsulfanyl)benzyl]methylamine (67% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07563908B2 |
| 出典データセット | uspto-grants-2009_07 |
| ORD ID | ord-b456a65a718c4ffea822d08d3e083a9a |
| 出典メモ | uspto-grants-2009_07 |