関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Phenylacetylene | HCID 10821 | — |
| 反応物 | Triphenylphosphine | HCID 11776 | — |
| 反応物 | 2-Bromo-5-iodopyrazine | HCID 21931200 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 2-Bromo-5-phenylethynyl-pyrazine | HCID 57516783 | 23.5% |
反応手順
To a solution of 2-bromo-5-iodopyrazine (500 mg, 1.76 mmol), phenylacetylene (224 mg, 241 μl, 2.19 mmol, 1.25 equiv.), triethylamine (533 mg, 734 μl, 5.27 mmol, 3 equiv.), bis(triphenylphosphine)palladium (II) chloride (73.9 mg, 0.105 mmol, 0.06 equiv.) and triphenyl-phosphine (13.8 mg, 0.053 mmol, 0.03 equiv.) in 10 ml of THF was added under an Argon atmosphere copper (I) iodide (10.0 mg, 0.053 mmol, 0.03 equiv.). The suspension was warmed to 60° C. overnight, taken up in 5 ml of ethyl acetate and adsorbed on 4 g of silica. Purification by flash chromatography on silicagel using a 2:1 ethyl acetate/heptane mixture yielded the title compound as a light brown solid (107 mg, 23% yield). The material was directly used in the next step without further characterization.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08420661B2 |
|---|
| 出典データセット | uspto-grants-2013_04 |
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| ORD ID | ord-e9173f20fead49e8a3042a7a6b9342f8 |
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| 出典メモ | uspto-grants-2013_04 |
|---|
