関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | N,N-Dimethylurea | HCID 11737 | — |
| 反応物 | 2-Chloro-4-((6-nitropyridin-3-yl)oxy)pyridine | HCID 59322779 | — |
| 触媒 | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| 触媒 | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 1,1-Dimethyl-3-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea | HCID 90410845 | 51.2% |
反応手順
A mixture of Example A1 (1 g, 3.97 mmol) in dioxane (20 mL) was sparged with Ar, treated with N,N-dimethyl urea (0.700 g, 7.95 mmol) and Cs2CO3 (1.942 g, 5.96 mmol), sparged with Ar, treated with dppf [1,1′-bis(diphenylphosphino)ferrocene] (12.38 g, 22.33 mmol) and Pd2(dba)3 (0.182 g, 0.199 mmol), sparged once again with Ar and heated at 95° C. overnight. The mixture was cooled to RT, treated with EtOAc and the solids removed via filtration through silica gel. The filtrate was concentrated to dryness and purified twice via silica gel chromatography (MeOH/DCM) to afford 1,1-dimethyl-3-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea (616 mg, 51%). MS (ESI) m/z: 304.1 (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 |
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| ORD ID | ord-3201dcc5150d41e88ce9e0c5933e6f3e |
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| 出典メモ | uspto-grants-2016_04 |
|---|
