関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 1-Ethynyl-4-(trifluoromethyl)benzene | HCID 4348295 | — |
| 反応物 | 5-Iodo-1-methyl-1H-pyrazole | HCID 13334065 | — |
| 触媒 | Triphenylphosphine | HCID 11776 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 1-Methyl-5-{[4-(trifluoromethyl)phenyl]ethynyl}-1H-pyrazole | HCID 86684863 | 80.5% |
反応手順
A mixture of 5-iodo-1-methyl-1H-pyrazole (8.00 g), 1-ethynyl-4-(trifluoromethyl)benzene (6.54 g), copper(I) iodide (110 mg), bis(triphenylphosphine)palladium(II) dichloride (1.35 g), triphenylphosphine (504 mg), triethylamine (8.00 mL) and dimethylformamide (70 mL) was stirred at 75° C. for 2 hours. Thereafter, the reaction solution was added to water, and the obtained mixture was then extracted with ethyl acetate. The organic layer was successively washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=85:15 to 75:25), so as to obtain the title compound (7.74 g) in the form of a yellow solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08642626B2 |
|---|
| 出典データセット | uspto-grants-2014_02 |
|---|
| ORD ID | ord-2746452428f0474e8b37d0e24d47a569 |
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| 出典メモ | uspto-grants-2014_02 |
|---|
