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Indole → 5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Indole | HCID 798 | — |
| 反応物 | Flurothyl | HCID 9528 | — |
| 反応物 | 3-Methyl-4-nitrophenol | HCID 17412 | — |
| 反応物 | Sodium hydride | HCID 24758 | — |
| 反応物 | Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate) | HCID 67942 | — |
| 反応物 | Phenolate | HCID 119047 | — |
| 溶媒 | Hexamethylphosphoramide | HCID 12679 | — |
| 生成物 | 5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid | HCID 57646517 | — |
反応手順
5-(2,2,2-trifluoroethoxy)-1H-indole-3-carboxylic acid was prepared following the procedure reported in Synthesis (1980) 727. 3-methyl-4-nitrophenol (Aldrich) was deprotonated with sodium hydride in HMPA, and the resulting phenolate alkylated with 2,2,2-trifluoroethyl tosylate (Aldrich). The resulting trifluoroethyl ether was then converted to the indole using the Batcho-Leimgruber protocol. Formylation and oxidation as described herein gave the title compound as an off-white solid. MS (m/e) 260.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09434724B2 |
| 出典データセット | uspto-grants-2016_09 |
| ORD ID | ord-4d827cc537484e228c849fdeaddc49cf |
| 出典メモ | uspto-grants-2016_09 |