| Identification | Back Directory | [Name]
Methyl 6-broMo-2-Methoxynicotinate | [CAS]
1009735-24-3 | [Synonyms]
Methyl 6-broMo-2-Methoxynicotinate
6-bromo-2-methoxynicotinic acid methyl ester
3-Pyridinecarboxylic acid, 6-bromo-2-methoxy-, methyl ester | [Molecular Formula]
C8H8BrNO3 | [MOL File]
1009735-24-3.mol | [Molecular Weight]
246.06 |
| Chemical Properties | Back Directory | [Boiling point ]
296.5±35.0 °C(Predicted) | [density ]
1.530±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [pka]
-3.08±0.10(Predicted) | [Appearance]
White to light yellow Solid |
| Hazard Information | Back Directory | [Synthesis]
Step 2: Synthesis of methyl 6-bromo-2-methoxynicotinate; To N,N-dimethylformamide (10 mL), potassium carbonate (1.34 g, 9.48 mmol), 6-bromo-2-methoxynicotinic acid (1.10 g, 4.74 mmol), and iodomethane (0.895 g, 6.31 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was diluted with water and ethyl acetate and the organic and aqueous layers were separated. The aqueous layer was extracted twice with ethyl acetate. All organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by silica gel column chromatography using 5%-10% ethyl acetate/heptane gradient elution to afford methyl 6-bromo-2-methoxynicotinate as a colorless oil (0.459 g, 40% yield).1H NMR (500 MHz, DMSO-d6) δppm3.81 (3H, s), 3.93 (3H, s), 7.36 (1H, d, J = 7.8 Hz), 8.06 (1H, d, J = 7.8 Hz). | [References]
[1] Patent: WO2010/116282, 2010, A1. Location in patent: Page/Page column 60
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4273 - 4288 |
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