|
|
| | 5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER Basic information |
| Product Name: | 5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER | | Synonyms: | 5-Bromo-1H-indazole-7-carboxylic acid methyl ester;Methyl 5-bromo-1H-indazole-7-carboxylate;1H-Indazole-7-carboxylic acid, 5-broMo-, Methyl ester;5-Bromo-7-(methoxycarbonyl)-1H-indazole;ethyl 5-broMo-1H-indazole-7-carboxylate;5-Bromo-1H-indazole-7-carboxylic;5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER | | CAS: | 898747-24-5 | | MF: | C9H7BrN2O2 | | MW: | 255.07 | | EINECS: | | | Product Categories: | | | Mol File: | Mol File |  |
| | 5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER Chemical Properties |
| Boiling point | 395.9±22.0 °C(Predicted) | | density | 1.709±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | pka | 10.67±0.40(Predicted) | | Appearance | Off-white to yellow Solid | | InChI | InChI=1S/C9H7BrN2O2/c1-14-9(13)7-3-6(10)2-5-4-11-12-8(5)7/h2-4H,1H3,(H,11,12) | | InChIKey | QQXHHJBRURQNLO-UHFFFAOYSA-N | | SMILES | N1C2=C(C=C(Br)C=C2C(OC)=O)C=N1 |
| RIDADR | 2811 | | HazardClass | 6.1 | | PackingGroup | Ⅲ | | HS Code | 2933998090 |
| | 5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER Usage And Synthesis |
| Synthesis | Methyl 2-amino-5-bromo-3-methylbenzoate (19-S3, 10.9 g, 44.7 mmol) and potassium acetate (AcOK, 1.32 g, 13.41 mmol) were dissolved in dichloromethane (CH2Cl2, 50 mL) under nitrogen protection and cooled to 0 °C. Acetic anhydride (Ac2O, 10.6 g, 103 mmol) was added slowly and the reaction mixture was stirred at room temperature for 1 hour. Subsequently, the mixture was heated to 60 °C and tert-butyl nitrite (t-BuONO, 10.2 g, 98.3 mmol) was added. The resulting mixture was continued to be stirred at 60 °C for 4 hours. After completion of the reaction, it was cooled to room temperature, the reaction was quenched with saturated aqueous sodium bicarbonate (NaHCO3) and extracted with ethyl acetate (EtOAc). The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=100:0 to 10:1) to afford methyl 5-bromo-1H-indazole-7-carboxylate (19-S4, 8.0 g, 70.5% yield) as a yellow solid. lc-MS (ESI) m/z: 255 (M+H). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2578 - 2581
[2] Patent: WO2018/160889, 2018, A1. Location in patent: Page/Page column 474; 475
[3] Patent: WO2015/157093, 2015, A1. Location in patent: Paragraph 0394
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1156 - 1162
[5] Patent: WO2008/65508, 2008, A1 |
| | 5-BROMO-7-INDAZOLECARBOXYLIC ACID METHYL ESTER Preparation Products And Raw materials |
|