関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 4-tert-Butylphenylboronic acid | HCID 2734320 | — |
| 反応物 | 7-(2-Bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester | HCID 69891158 | — |
| 触媒 | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 7-[(4'-Tert-butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester | HCID 69891466 | 87.5% |
反応手順
To 5 ml dioxane was added in sequence, 7-(2-bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester (100 mg, 0.25 mmol), potassium carbonate (0.25 ml of 2.0M aqueous solution, 0.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene (6.9 mg, 0.0125 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (10.2 mg, 0.0125 mmol) and 4-tert-butylbenzeneboronic acid (111.5 mg, 0.63 mmol). The resulting mixture was degassed and placed under a nitrogen atmosphere. The degassing procedure was repeated 5 times and the reaction mixture was heated under reflux under nitrogen overnight. The reaction mixture was then cooled to room temperature and poured into water. The aqueous mixture was extracted with ethyl acetate and the ethyl acetate solution was washed with brine, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was purified by preparative thick layer chromatography, eluting with 60:40 hexane/ethyl acetate to yield the title compound (99 mg, 87.3% yield).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US06713489B2 |
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| 出典データセット | uspto-grants-2004_03 |
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| ORD ID | ord-eb795fd21c0d4831bfb772b80a48ee85 |
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| 出典メモ | uspto-grants-2004_03 |
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