関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | 1,4-Dioxane | HCID 31275 | — |
| 反応物 | Trimethylsilylacetylene | HCID 66111 | — |
| 反応物 | 2-Pyridinamine, 5-bromo-6-methyl- | HCID 170678 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 6-Methyl-5-trimethylsilanylethynyl-pyridin-2-ylamine | HCID 59255232 | 68.5% |
反応手順
To a mixture of 6-amino-3-bromo-2-methylpyridine (200 mg, 1.0 mmol), trimethylsilylacetylene (0.22 mL, 1.6 mmol), copper (I) iodide (9.9 mg, 0.052 mmol), and 1,4-dioxane (1.5 mL) was added bis(triphenylphosphine)palladium (II) chloride (73 mg, 0.10 mmol), which was stirred under nitrogen atmosphere for 3 hours and 30 minutes at 100° C. The reaction mixture was allowed to room temperature, water was added to the reaction mixture at the same temperature, ethyl acetate was added, and the mixture was filtered through a Celite pad. The organic layer of the filtrate was separated and washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure, and the residue thus obtained was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (140 mg, 57%, purity: 86%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07691882B2 |
|---|
| 出典データセット | uspto-grants-2010_04 |
|---|
| ORD ID | ord-4a4737664898482ca5c07efeed9c36d1 |
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| 出典メモ | uspto-grants-2010_04 |
|---|
