関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | 1-Methylpiperidine-4-carboxamide | HCID 339011 | — |
| 反応物 | 2-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine | HCID 59322779 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 触媒 | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | HCID 11155794 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 1-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperidine-4-carboxamide | HCID 90410853 | 56.3% |
反応手順
A mixture of Example A1 (0.25 g, 0.994 mmol), Cs2CO3 (0.486 g, 1.490 mmol), 1-methylpiperidine-4-carboxamide (0.155 g, 1.093 mmol), and X-phos (0.024 g, 0.050 mmol) in dioxane (5 mL) was sparged with Ar, treated with Pd2(dba)3 (0.045 g, 0.050 mmol) and heated at 90° C. overnight. Additional X-phos (17 mg) and Pd2(dba)3 (30 mg) were added and the mixture heated at 90° C. for 7 h. The mixture was cooled to RT, treated with water and extracted with EtOAc (3×). The combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 1-methyl-N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)piperidine-4-carboxamide (200 mg, 56%). MS (ESI) m/z: 358.2 (M+H+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09309224B2 |
|---|
| 出典データセット | uspto-grants-2016_04 |
|---|
| ORD ID | ord-0845a84a8fe1403d90b87b4f790ca1ea |
|---|
| 出典メモ | uspto-grants-2016_04 |
|---|
