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4-Bromo-2-nitroaniline → tert-butyl 4-(4-amino-3-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 4-Bromo-2-nitroaniline | HCID 70132 | — |
| 反応物 | Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 4642098 | — |
| 反応物 | Tripotassium phosphate trihydrate | HCID 18407952 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | tert-butyl 4-(4-amino-3-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate | HCID 59843222 | 75% |
反応条件
| 温度 | 110 °C |
|---|
反応手順
To a degassed mixture of 4-bromo-2-nitroaniline (1 g, 4.6 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.42 g, 4.6 mmol), tripotassium phosphate trihydrate (3.9 g, 14.64 mmol) in dioxane and water (30 mL, 8:1) was added Pd(dppf)2Cl2 (337 g, 0.46 mmol). The mixture was refluxed at 110° C. for 3 hours. Filtration and concentration gave crude product, which was purified by silica gel column chromatography to afford the title compound (1.1 g, yield: 75%). MS (ESI): 320 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US09434697B2 |
| 出典データセット | uspto-grants-2016_09 |
| ORD ID | ord-413bdf926a4947f88b057a03eb098fee |
| 出典メモ | uspto-grants-2016_09 |