関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 4912908 | — |
| 反応物 | Methyl 4-bromofuran-2-carboxylate | HCID 12239443 | — |
| 触媒 | HCID 178418851 | HCID 178418851 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 2-Furancarboxylic acid, 4-(1-methyl-1H-pyrazol-5-yl)-, methyl ester | HCID 57826572 | 26.2% |
反応手順
A solution of methyl 4-bromo-2-furancarboxylate (470 mg, 2.29 mmol), potassium carbonate (1.58 g, 11.46 mmol), 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (525 mg, 2.52 mmol) [prepared according to Preparation 7] and bis(tri-t-butylphosphine)palladium(0) (58.6 mg, 0.115 mmol) in 1,4-Dioxane (9.5 ml) and water (1.9 ml) was stirred at 80° C. in a sealed tube for 1 h. The solution was partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (30% EtOAc in hexanes) affording methyl 4-(1-methyl-1H-pyrazol-5-yl)-2-furancarboxylate (124 mg, 0.60 mmol, 26% yield) as a white powder: LCMS (ES) m/e 206 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08946278B2 |
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| 出典データセット | uspto-grants-2015_02 |
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| ORD ID | ord-9519a91bb74f4980893f6b109b5fef6d |
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| 出典メモ | uspto-grants-2015_02 |
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