関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dichloromethane | HCID 6344 | — |
| 反応物 | 2,6-Difluorophenylboronic acid | HCID 2734336 | — |
| 反応物 | 6-Bromo-2-methyl-3-nitropyridine | HCID 24728014 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | Sodium Carbonate | HCID 10340 | — |
| 溶媒 | 1,4-Dioxane | HCID 31275 | — |
| 生成物 | 6-(2,6-Difluorophenyl)-2-methyl-3-nitropyridine | HCID 67958235 | 56% |
反応手順
A suspension of 2-bromo-6-methyl-5-nitropyridine (3 g, 13.82 mmol, Matrix Scientific), 2,6-difluorobenzeneboronic acid (4.37 g, 27.6 mmol, Alfa Aesar) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with DCM (0.564 g, 0.691 mmol, Strem) in Dioxane (60 mL) (degassed with argon for 30 min) and Na2CO3, 2.0 M (20.74 mL, 41.5 mmol) was heated to 100° C. under N2. After 3 h, 2,6-difluorobenzeneboronic acid (4.37 g, 27.6 mmol) was further added. After a total of 7 h, 2,6-difluorobenzeneboronic acid (2.18 g, 13.8 mmol) was further added. After a total of 9 h, the reaction mixture was cooled to 23° C., diluted with EtOAc (400 ml) and washed with brine (200 mL), dried over MgSO4, concentrated in vacuo and purified by silica gel chromatography (eluent: 5-10% EtOAc/hexane), affording 6-(2,6-difluorophenyl)-2-methyl-3-nitropyridine (1.931 g, 56%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09090593B2 |
|---|
| 出典データセット | uspto-grants-2015_07 |
|---|
| ORD ID | ord-07ddec78a2fc438a849269ed09293510 |
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| 出典メモ | uspto-grants-2015_07 |
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