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| | methyl 6-amino-3,5-dibromopicolinate Basic information |
| Product Name: | methyl 6-amino-3,5-dibromopicolinate | | Synonyms: | Methyl 6-aMino-3,5-dibroMopyridine-2-carboxylate;6-Amino-3,5-dibromopyridine-2-carboxylic acid methyl ester;methyl 6-amino-3,5-dibromopicolinate;2-Pyridinecarboxylic acid, 6-amino-3,5-dibromo-, methyl ester | | CAS: | 443956-21-6 | | MF: | C7H6Br2N2O2 | | MW: | 309.94 | | EINECS: | | | Product Categories: | | | Mol File: | 443956-21-6.mol |  |
| | methyl 6-amino-3,5-dibromopicolinate Chemical Properties |
| Boiling point | 366.0±37.0 °C(Predicted) | | density | 1.997 | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | pka | -0.94±0.10(Predicted) | | Appearance | Light yellow to yellow Solid |
| | methyl 6-amino-3,5-dibromopicolinate Usage And Synthesis |
| Uses | Methyl 6-Amino-3,5-dibromopyridine-2-carboxylate is used as a reagent in the synthesis of imidazopyridines as Syk inhibitors. Also used as a reagent in the synthesis of quinoline, quinoxaline and naphthyridine derivatives as antibacterial agents. | | Synthesis | General procedure for the synthesis of methyl 6-amino-3,5-dibromopyridine-2-carboxylate, methyl 6-amino-3-bromopyridine-2-carboxylate, and methyl 5-bromo-6-aminopyridine-2-carboxylate from methyl 6-aminopyridine-2-carboxylate: over a period of 30 min, a solution of chloroform (40 mL) with bromine (2.57 mL) was added slowly and dropwise to methyl 6-aminopyridine-2-carboxylate ( 6.92 g) in a solution of chloroform (300 mL). The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the mixture was upsampled onto a silica gel column and purified by column chromatography (SiO2, heptane/ethyl acetate) to isolate three products: methyl 6-amino-5-bromo-pyridine-2-carboxylate (2 g, 19% yield), methyl 6-amino-3-bromo-pyridine-2-carboxylate (3 g, 29% yield) and methyl 6-amino-3,5-dibromopyridine-2-carboxylate (2.6 g, 18% yield).The 1H NMR (400 MHz, chloroform-d) data for methyl 6-amino-5-bromopyridine-2-carboxylate were as follows: δ 3.97 (s, 3H), 5.22 (br.s, 2H), 7.38 (d, J = 7.8 Hz, 1H), 7.79 (d, J = 7.8 Hz, 1H). | | References | [1] Patent: WO2011/75591, 2011, A1. Location in patent: Page/Page column 95
[2] Patent: US2011/152312, 2011, A1. Location in patent: Page/Page column 40 |
| | methyl 6-amino-3,5-dibromopicolinate Preparation Products And Raw materials |
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