関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Tetrahydrofuran | HCID 8028 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 9-Borabicyclo(3.3.1)nonane | HCID 78966 | — |
| 反応物 | 2,6-Dimethyl-3-nitropyridine | HCID 84958 | — |
| 反応物 | Piperidine, 1-methyl,4-methylene- | HCID 139537 | — |
| 触媒 | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 2-Methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridine | HCID 58476617 | 11.5% |
反応手順
To a solution of 9-BBN in THF (0.5 M, 4.93 mL, 2.46 mmol) was added 1-methyl-4-methylenepiperidine (274 mg, 2.46 mmol). The reaction mixture was allowed to stir at 75° C. for 1 h and was then allowed to cool to rt. The resulting solution was transferred into a solution of 2-methyl-5-nitro-6-methylpyridine (486 mg, 2.24 mmol) in DMF (11 mL). To the mixture were added [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1:1 complex with DCM, 54.9 mg, 0.0672 mmol) and potassium carbonate (402 mg, 2.91 mmol). The reaction mixture was allowed to stir for 3 h at rt. The mixture was quenched by the addition of water (10 mL). The aqueous solution was extracted with DCM. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 2-methyl-6-[(1-methylpiperidin-4-yl)-methyl]-3-nitropyridine (64 mg, 10%) as a white solid. LCMS (FAL): Rt=3.38 min, m/z=250.2 (M+H).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08268992B2 |
|---|
| 出典データセット | uspto-grants-2012_09 |
|---|
| ORD ID | ord-2ac7720623b243bd8e0ebd4f06f23dfc |
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| 出典メモ | uspto-grants-2012_09 |
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