参与物
| 角色 | 名称 | HCID | 投料 |
|---|
| 反应物 | 二异丙胺 | HCID 7912 | — |
| 反应物 | 2,3-二氟苯硼酸 | HCID 2734333 | — |
| 反应物 | 三苯基膦三间磺酸钠盐 | HCID 6099338 | — |
| 反应物 | 5-Bromo-1-(2-methoxyethyl)-3-nitropyridin-2(1H)-one | HCID 22293279 | — |
| 催化剂 | palladium acetate | HCID 167845 | — |
| 溶剂 | 聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] | HCID 962 | — |
| 溶剂 | N,N-二甲基甲酰胺 | HCID 6228 | — |
| 产物 | 5-(2,3-Difluorophenyl)-1-(2-methoxyethyl)-3-nitropyridin-2(1H)-one | HCID 22293173 | 59.7% |
反应步骤
Palladium acetate (41.0 mg, 0.18 mmol) was added to a solution of 5-bromo-1-(2-methoxyethyl)-3-nitropyridin-2(1H)-one (500 mg, 1.81 mmol), 2,3-difluorophenyl boronic acid (570 mg, 3.61 mmol), diisopropylamine (0.759 mL, 5.41 mmol) and 3,3′,3″-phosphinidynetris(benzenesulfonic acid) trisodium salt (310 mg, 0.541 mmol), in N,N-dimethylformamide (15 mL) and water (5 mL) and heated to 80° C. After 2 h, the mixture was allowed to cool to ambient temperature and filtered. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (335 mg). MS 311 (M+1). 1H NMR (500 MHz, CDCl3) δ 8.56 (d, J=2.7 Hz, 1H), 8.03 (d, J=2.4 Hz, 1H), 7.23-7.18 (m, 2H), 7.15-7.12 (m, 1H), 4.33 (t, J=4.8 Hz, 2H), 3.74 (t, J=4.8 Hz, 2H), 3.35 (s, 3H).
来源与证据
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 专利号 | US07745427B2 |
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| 来源数据集 | uspto-grants-2010_06 |
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| ORD ID | ord-603d6f3f4e5349fbacc3acff1172a14e |
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| 来源说明 | uspto-grants-2010_06 |
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