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| | Ethyl 2-forMylisonicotinate Basic information |
| Product Name: | Ethyl 2-forMylisonicotinate | | Synonyms: | Ethyl 2-forMylisonicotinate;2-forMyl-pyridine-4-carboxylic acid 4-ethyl ester;ethyl 2-formylpyridine-4-carboxylate;108630;4-Pyridinecarboxylic acid, 2-formyl-, ethyl ester;2-formyl-4-Pyridinecarboxylic acid ethyl ester | | CAS: | 21908-08-7 | | MF: | C9H9NO3 | | MW: | 179.17 | | EINECS: | | | Product Categories: | | | Mol File: | 21908-08-7.mol |  |
| | Ethyl 2-forMylisonicotinate Chemical Properties |
| Boiling point | 288.3±25.0 °C(Predicted) | | density | 1.204±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 1.20±0.10(Predicted) | | Appearance | White to light yellow Solid |
| | Ethyl 2-forMylisonicotinate Usage And Synthesis |
| Uses | Ethyl 2-Formylisonicotinate is an intermediate used to synthesize aminoisoindoles as BACE1 inhibitors exhibiting in vivo brain reduction of β-amyloid peptides. It is also used to prepare arylmethylamino analogs of edotecarin as topoisomerase I inhibitors with antitumor activities. | | Synthesis | General procedure for the synthesis of ethyl 2-formylpyridine-4-carboxylate from ethyl 2,4-pyridinedicarboxylate: to an anhydrous solution of diethylpyridine-2,4-dicarboxylate (20.0 g, 89.6 mmol) in anhydrous tetrahydrofuran (300 mL) was added slowly and dropwise at -78 °C aluminum diisobutyl hydroxide (134.4 mL, 134.4 mmol, 1 mol/L in toluene). After the dropwise addition was completed, the reaction mixture was continued to be stirred at -78°C for 3 hours. Subsequently, the reaction solution was slowly poured into a pre-cooled mixture of acetic acid (50 mL) and water (250 mL) and gradually warmed to room temperature. After continued stirring for 1.5 h, the pH of the mixture was adjusted to 8 with sodium bicarbonate solution at 0 °C. Extraction was carried out with ethyl acetate (500 mL x 5), and the organic layers were combined and dried over anhydrous sodium sulfate and subsequently concentrated. Purification by silica gel column chromatography (petroleum ether: ethyl acetate = 40:1-10:1) afforded the target product ethyl 2-formylisonicotinate (13.0 g, 81% yield). lCMS m/z 180. | | References | [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 21, p. 9346 - 9361,16
[2] Patent: WO2016/130396, 2016, A1. Location in patent: Paragraph 0090; 0093; 0094
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1388 - 1409
[4] Collection of Czechoslovak Chemical Communications, 1998, vol. 63, # 2, p. 199 - 204 |
| | Ethyl 2-forMylisonicotinate Preparation Products And Raw materials |
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