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HRID 471970作成日：2026年10月25日
Dimethylformamide → 3-[5-(7-azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine
https://huagongshe.com/reaction/471970
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | N,N-Dimethylpropargylamine | HCID 81643 | — |
| 反応物 | 7-(3-Bromo-4-nitrophenyl)-7-azabicyclo[2.2.1]heptane | HCID 57516846 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 3-[5-(7-azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine | HCID 58478633 | 79.5% |
反応手順
To 7-(3-bromo-4-nitro-phenyl)-7-azabicyclo[2.2.1]heptane (500 mg, 1.68 mmol), Pd(PPh3)2Cl2 (59 mg, 0.08 mmol), and CuI (10 mg, 0.05 mmol) were added DMF (5 mL), triethylamine (5 mL), and N,N-dimethylprop-2-yn-1-amine (420 mg, 538 μL, 5.05 mmol) under N2 atmosphere. The reaction was heated under microwave irradiation for 10 min at 100° C. The reaction mixture was diluted with ethyl acetate, washed with 50% saturated NaHCO3 (2×20 mL), water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to a red solid. Purification by silica gel chromatography (0-50% dichloromethane/ethyl acetate) provided 3-[5-(7-Azabicyclo[2.2.1]heptan-7-yl)-2-nitro-phenyl]-N,N-dimethyl-prop-2-yn-1-amine (400 mg, 79% yield). LC/MS m/z 300.5 [M+H]+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08633189B2 |
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| 出典データセット | uspto-grants-2014_01 |
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| ORD ID | ord-4f4c3969e1e94ba48af0185bb8e3fe30 |
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| 出典メモ | uspto-grants-2014_01 |
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