関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Lithium Chloride | HCID 433294 | — |
| 反応物 | 4-(Triethylsilyl)-3-butyn-1-ol | HCID 2760694 | — |
| 反応物 | 5-Chloro-2-iodo-4-methylaniline | HCID 58475405 | — |
| 触媒 | Palladium Chloride | HCID 24290 | — |
| 触媒 | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 2-(6-chloro-5-methyl-2-(triethylsilyl)-1H-indol-3-yl)ethanol | HCID 66832034 | 79.2% |
反応手順
5-chloro-2-iodo-4-methylaniline (1.50 g; 5.61 mmol), 4-(triethylsilyl)but-3-yn-1-ol (2.36 mL; 11.22 mmol), Bis(diphenylphosphino)ferrocene]palladium(II) chloride (0.229 g; 0.280 mmol), lithium chloride (0.237 g; 5.61 mmol) and sodium carbonate (1.19 g; 11.22 mmol) were suspended in DMF (14 mL) and the mixture was stirred at 100° C. for 15 hours. The mixture was concentrated under reduced pressure and diluted in ethyl acetate. The organic layer was successively washed with brine, sodium thiosulphate, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to afford 1.44 g (79%) of the title compound as a brown oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US09434722B2 |
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| 出典データセット | uspto-grants-2016_09 |
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| ORD ID | ord-cf662b2f82ea4046ac3dbaf33facd596 |
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| 出典メモ | uspto-grants-2016_09 |
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