関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Indole | HCID 798 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 1,4-Dioxane | HCID 31275 | — |
| 反応物 | Methylboronic Acid | HCID 139377 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 4,6-dimethyl-1H-indole-3-carboxylic acid | HCID 82404736 | 40.9% |
反応手順
A mixture of indole 5 (690 mg, 3.28 mmol), methylboronic acid (495 mg, 3.94 mmol, 1.2 eq.), Pd(dppf)Cl2 (180 mg, 0.656 mmol, 0.2 eq.) and Cs2CO3 (3.20 g, 9.84 mmol, 3.0 eq.) in dioxane (21 mL) and water (3 mL) was stirred at 110° C. overnight under N2. The mixture was diluted with water and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (petroleum ether/EtOAc=5/1) to give the desired product (170 mg, 1.17 mmol, 40.9%) as a white solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09434724B2 |
|---|
| 出典データセット | uspto-grants-2016_09 |
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| ORD ID | ord-863bbacc59ae4f1498b0036fe5995fc5 |
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| 出典メモ | uspto-grants-2016_09 |
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