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Aniline → 5-(phenylamino)-N-(2-(piperidin-1-yl)phenyl)furan-2-carboxamide
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Aniline | HCID 6115 | — |
| 反応物 | Binap, (A+-)- | HCID 634876 | — |
| 反応物 | 5-bromo-N-(2-piperidin-1-ylphenyl)furan-2-carboxamide | HCID 889132 | — |
| 反応物 | Potassium tert-butoxide | HCID 23665647 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 5-(phenylamino)-N-(2-(piperidin-1-yl)phenyl)furan-2-carboxamide | HCID 44444584 | 40% |
反応手順
To a solution of 5-bromo-furan-2-carboxylic acid (2-piperidin-1-yl-phenyl)-amide (1.0 mmol) in toluene (7.5 mL) was added aniline (1.3 mmol), tris(dibenzylidineacetone)dipalladium(0) (“Pd2 dba”) (Aldrich) (0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (“BINAP”) (0.1 mmol), and potassium tert-butoxide (“t-BuOK”) (1.5 mmol), and the resulting mixture was refluxed overnight. The reaction was then cooled to room temperature, passed through a plug of silica and concentrated. Purification of the dark brown residue by HPLC afforded the product. Yield: 40%. MS: 362 (M+1).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07790724B2 |
| 出典データセット | uspto-grants-2010_09 |
| ORD ID | ord-aff70afe3b164deb83421fc515bb1c33 |
| 出典メモ | uspto-grants-2010_09 |