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Benzaldehyde → rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-phenyl-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Benzaldehyde | HCID 240 | — |
| 反応物 | alpha-Ethynylbenzenemethanol | HCID 20155 | — |
| 反応物 | (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 18359254 | — |
| 反応物 | HCID 178462451 | HCID 178462451 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Triethylamine | HCID 8471 | — |
| 生成物 | rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-phenyl-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one | HCID 9969383 | — |
反応手順
Using Method D above, 3-hydroxy-3-phenyl-1-propyne (0.1 g, 0.78 mmol) (prepared by the addition of ethynylmagnesium chloride (Aldrich) to benzaldehyde (Aldrich) through Method A above) was coupled to (Z)-4-bromo-1,3-dihydro-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one (0.1 g, 0.31 mmol) (Starting Material 1) using DPPFPdCl2 (12.6 mg) (Aldrich) and CuI (3 mg) (Aldrich) as catalyst in DMF (5 mL) and Et3N (5 mL) as solvent at 85° C. for 18 h, yielding rac-(Z)-1,3-dihydro-4-(3-hydroxy-3-phenyl-1-propynyl)-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 42 mg, 38%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US06313310B1 |
| 出典データセット | uspto-grants-2001_11 |
| ORD ID | ord-023af678f9a34135891f01370728af4e |
| 出典メモ | uspto-grants-2001_11 |