関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Tetrahydrofuran | HCID 8028 | — |
| 反応物 | Ammonium Chloride | HCID 25517 | — |
| 反応物 | 1-Fluoro-3-iodobenzene | HCID 70725 | — |
| 反応物 | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| 反応物 | Ethyl 5-((trimethylsilyl)ethynyl)nicotinate | HCID 67047749 | — |
| 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 | 5-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester | HCID 67047762 | 80% |
反応手順
Add a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.88 g, 3.38 mmol) to a mixture of 3-iodofluorobenzene (0.50 g, 2.25 mmol), 5-trimethylsilanylethynyl-nicotinic acid ethyl ester (0.84 g, 3.38 mmol), (prepared essentially as described in PREPARATION 16), bis(triphenylphosphine)palladium (II) dichloride (0.03 g, 0.05 mmol) and copper (I) iodide (0.02 g, 0.09 mmol) at −780C. Warm to room temperature, stir overnight and dilute the mixture with ethyl acetate and an aqueous saturated solution of ammonium chloride. Separate the organic layer; dry (magnesium sulfate), filter and concentrate. Purify the resulting residue by silica gel chromatography, eluting with 2.5:45:52.5 ethyl acetate:chloroform:hexanes, to give the title compound as a pale yellow solid (0.46 g, 80%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07915424B2 |
|---|
| 出典データセット | uspto-grants-2011_03 |
|---|
| ORD ID | ord-a0fe3f254a904a1c9d2c2616b051a16f |
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| 出典メモ | uspto-grants-2011_03 |
|---|
