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| | 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester Basic information | | Uses |
| Product Name: | 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester | | Synonyms: | 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester;Ethyl 7-azaindole-2-carboxylate;1H-Prrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester;2-(Ethoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine;ethyl 1H-pyrrolo[2,3-b]pyridine-2-carbo×ylate;ethyl 1H-pyrrolo[2;ethyl1H-pyrrolo[2,3-b]pyridine-2-carbo;2-(Ethoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine, Ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate | | CAS: | 221675-35-0 | | MF: | C10H10N2O2 | | MW: | 190.2 | | EINECS: | | | Product Categories: | Heterocycle-Pyridine series | | Mol File: | 221675-35-0.mol | ![1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester Structure](CAS/GIF/221675-35-0.gif) |
| | 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester Chemical Properties |
| Boiling point | 436.4±37.0 °C(Predicted) | | density | 1.27±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 5.73±0.40(Predicted) | | Appearance | Off-white to yellow Solid | | InChI | InChI=1S/C10H10N2O2/c1-2-14-10(13)8-6-7-4-3-5-11-9(7)12-8/h3-6H,2H2,1H3,(H,11,12) | | InChIKey | CBIVEMGUNRNUEB-UHFFFAOYSA-N | | SMILES | C12NC(C(OCC)=O)=CC1=CC=CN=2 |
| | 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester Usage And Synthesis |
| Uses | 1H-pyrrolo[2,3-B]pyridine-2-carboxylic acid ethyl ester is an important raw material in organic synthesis. Its derivative, pyrrolopyridine-2-carboxamide, is a glycogen phosphorylase inhibitor used to prevent or treat diabetes, hypertension, hypercholesterolemia, hyperinsulinemia, hyperlipidemia, atherosclerosis, or tissue ischemia, and can also be used as a cardioprotective agent. | | Synthesis | General procedure for the synthesis of ethyl 1H-pyrrolo[2,3-B]pyridine-2-carboxylate from compound (CAS: 287384-79-6): compound 29 (9.7 g, 31.4 mmol, 1 equiv.) was dissolved in 6 N hydrochloric acid solution (50 mL) and stirred for 2 hr at 50 °C, followed by continued stirring at room temperature overnight. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 13 with solid potassium carbonate (K2CO3), followed by extraction with ethyl acetate (EtOAc). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 30 (6.0 g, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 11.12 (br s, 1H), 8.59 (d, J = 4.8 Hz, 1H), 8.05 (dd, J = 8.0, 1.6 Hz, 1H), 7.19 (s, 1H), 7.18-7.15 (m, 1H), 4.46 (q, J = 6.8 Hz. 2H), 1.44 (t, J = 6.8 Hz, 3H). | | References | [1] European Journal of Medicinal Chemistry, 2014, vol. 88, p. 3 - 9
[2] Patent: WO2015/187428, 2015, A1. Location in patent: Paragraph 00502; 00505; 00506
[3] Patent: US2009/318455, 2009, A1. Location in patent: Page/Page column 69; 93 |
| | 1H-Pyrrolo[2,3-b]pyridine-2-carboxylic acid, ethyl ester Preparation Products And Raw materials |
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