関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | N,N-Dimethylpropargylamine | HCID 81643 | — |
| 反応物 | 2-Bromo-4-fluoro-1-nitrobenzene | HCID 2756993 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 生成物 | 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine | HCID 67537237 | 68% |
反応手順
To a flask charged with N,N-dimethylprop-2-yn-1-amine (737 mg, 945 μL, 8.86 mmol), 2-bromo-4-fluoro-1-nitrobenzene (1300 mg, 5.91 mmol), PdCl2(PPh3)2 (415 mg, 0.59 mmol), CuI (169 mg, 0.89 mmol) were added triethylamine (2.47 mL, 17.73 mmol) and DMF (10 mL) under N2 atmosphere. The reaction mixture was heated at 60° C. for 5 h, then poured into water (300 mL) and extracted with ethyl acetate (3×40 mL). The organic fractions were combined, dried over MgSO4, filtered, and concentrated in vacuo. Purification by silica gel chromatography (50-100% ethyl acetate/hexanes) yielded 3-(4-fluoro-2-nitrophenyl)-N,N-dimethylprop-2-yn-1-amine (895 mg, 68% yield). LC/MS m/z 223.0 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08367660B2 |
|---|
| 出典データセット | uspto-grants-2013_02 |
|---|
| ORD ID | ord-9dfeda01c4f647f5b767728a06bf0e0c |
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| 出典メモ | uspto-grants-2013_02 |
|---|
