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Ethyl Acetate → 2'-Dimethylaminomethylbiphenyl-4-ylamine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 2-bromo-N,N-dimethylbenzylamine | HCID 74792 | — |
| 反応物 | 4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline | HCID 2734620 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | 1-Butanol | HCID 263 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 2'-Dimethylaminomethylbiphenyl-4-ylamine | HCID 58897692 | 51.8% |
反応手順
To a solution of 2-dimethylaminomethyl-bromobenzene (588 mg, 2.75 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (560 mg, 2.56 mmol) in toluene (10 mL) and n-BuOH (3 mL), Cs2CO3 (2.50 g, 7.67 mmol) in H2O (5 mL) was added, followed by addition of Pd(Ph3P)4 (200 mg, 0.17 mmol, 6%). The mixture was then heated at reflux for 4 h. EtOAc and H2O were added. The organic layer was separated, filtered, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel flash column using 50% EtOAc/hexanes (containing 1% TEA) as eluent to give a solid (300 mg). MS 182.0 (M—Me2N).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07678913B2 |
| 出典データセット | uspto-grants-2010_03 |
| ORD ID | ord-da1e68709173428f9a05daab3eea05ba |
| 出典メモ | uspto-grants-2010_03 |