関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 5-Chloropyridin-3-yl trifluoromethanesulfonate | HCID 15185870 | — |
| 反応物 | 4-Ethynyl-1-fluoro-2-methylbenzene | HCID 16213797 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178419050 | HCID 178419050 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 3-Chloro-5-(4-fluoro-3-methylphenylethynyl)-pyridine | HCID 67047801 | 44% |
反応手順
Add 4-ethynyl-1-fluoro-2-methylbenzene (0.56 g, 4.21 mmol), triethylamine (2.2 mL, 15 mmol), copper (I) iodide (36 mg, 0.19 mmol), and bis(triphenylphosphine)palladium (II) dichloride (110 mg, 0.15 mmol) to a solution of trifluoromethanesulfonic acid 5-chloropyridin-3-yl ester, (prepared as described in PREPARATION 25), (1.0 g, 3.8 mmol) in ethyl acetate (5 mL) under nitrogen. Heat the at 70° C. for 16 h and concentrate. Purify by silica gel chromatography, eluting with 100% dichloromethane, followed by a second silica gel chromatography eluting with 50:50 to 60:40 dichloromethane:hexanes, to give the title compound as a light yellow solid (410 mg, 44%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07915424B2 |
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| 出典データセット | uspto-grants-2011_03 |
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| ORD ID | ord-111deb5bc23f43d6822ed2d4aef65921 |
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| 出典メモ | uspto-grants-2011_03 |
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