関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Potassium cyclopropyltrifluoroborate | HCID 23697338 | — |
| 反応物 | 5-Bromo-6-(1,1,1-trifluoropropan-2-yloxy)picolinic acid | HCID 71087582 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 触媒 | Butyl-1-adamantylphosphine | HCID 68995490 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | 5-Cyclopropyl-6-(1,1,1-trifluoropropan-2-yloxy)picolinic acid | HCID 71087435 | 79% |
反応手順
5-Bromo-6-(1,1,1-trifluoropropan-2-yloxy)picolinic acid (2 g, 6.37 mmol), potassium cyclopropyltrifluoroborate (952 mg, 6.43 mmol), cesium carbonate (6.22 g, 19.1 mmol) and palladium(II)acetate (28.6 mg, 127 μmol) were suspended in toluene (55 mL) and water (6.11 mL) under an argon atmosphere. Butyl-1-adamantylphosphin (68.5 mg, 191 μmol) was added, the reaction mixture was heated to 120° C. for 1 d, poured onto icewater/1N HCl (150 mL) and extracted with EtOAc (2×300 mL). The combined organic layers were washed with icewater/brine (150 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (1.38 g, 79%) as a yellow solid. MS (EI): m/e=276.2 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09321727B2 |
|---|
| 出典データセット | uspto-grants-2016_04 |
|---|
| ORD ID | ord-ae0dddf6dcb44928a58fb06af65a7bda |
|---|
| 出典メモ | uspto-grants-2016_04 |
|---|
