|
|
| | 5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester Basic information |
| Product Name: | 5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester | | Synonyms: | Methyl 5-broMo-3-chloropyridine-2-carboxylate;5-Bromo-3-chloro-2-(methoxycarbonyl)pyridine, Methyl 5-bromo-3-chloropicolinate;5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester;3-chloro-5-bromo-pyridine-2-carboxylic acid methyl ester;2-Pyridinecarboxylic acid, 5-bromo-3-chloro-, methyl ester;5-Bromo-3-Chloropyridinecarboxylic acid methyl ester;Methyl 5-broMo-3-chloropicolinate | | CAS: | 1214336-41-0 | | MF: | C7H5BrClNO2 | | MW: | 250.48 | | EINECS: | 810-921-7 | | Product Categories: | | | Mol File: | 1214336-41-0.mol |  |
| | 5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester Chemical Properties |
| Boiling point | 311℃ | | density | 1.684 | | Fp | 142℃ | | storage temp. | Inert atmosphere,Room Temperature | | pka | -3.26±0.10(Predicted) | | form | crystalline powder | | color | White | | InChI | InChI=1S/C7H5BrClNO2/c1-12-7(11)6-5(9)2-4(8)3-10-6/h2-3H,1H3 | | InChIKey | QBNSPYFGGCZDJG-UHFFFAOYSA-N | | SMILES | C1(C(OC)=O)=NC=C(Br)C=C1Cl |
| | 5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester Usage And Synthesis |
| Uses | 5-Bromo-3-chloro-2-pyridinecarboxylic Acid Methyl Ester is an intermediate used to prepare aminopyridinyldihydrooxazine derivatives for use as BACE-1 and/or BACE-2 inhibitors. | | Synthesis | To a solution of dichloromethane (700 mL) containing traces of turbid 5-bromo-3-chloropyridine-2-carboxylic acid (60 g, 183.2 mmol), N,N-dimethylformamide (1 mL) and oxalyl chloride (24.9 mL, 286.9 mmol) were added slowly and dropwise. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the resulting yellow solution was cooled to 10 °C and methanol (30.8 mL, 761.3 mmol) was slowly added dropwise at this temperature, keeping the reaction temperature between 15 °C and 20 °C. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature overnight. At the end of the reaction, the reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution, followed by washing the organic layer with brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give methyl 5-bromo-3-chloro-2-pyridinecarboxylate (55 g) as a yellow solid, which could be used in the next reaction without further purification.LCMS (Method B): m/z 250/252/254 (M + 1), retention time 1.12 min. | | References | [1] Patent: WO2015/160636, 2015, A1. Location in patent: Page/Page column 164
[2] Patent: WO2015/160634, 2015, A1. Location in patent: Page/Page column 145
[3] Patent: WO2016/46071, 2016, A1. Location in patent: Page/Page column 61
[4] Patent: WO2016/87265, 2016, A1. Location in patent: Page/Page column 62; 63
[5] Patent: WO2016/87257, 2016, A1. Location in patent: Page/Page column 67-68 |
| | 5-Bromo-3-chloro-2-pyridinecarboxylic acid methyl ester Preparation Products And Raw materials |
|