| Identification | Back Directory | [Name]
5-Bromo-2-methyl-3-nitropyridine | [CAS]
911434-05-4 | [Synonyms]
5-broMo-2-Methyl-3-n
5-Bromo-3-nitropicoline
5-Bromo-3-nitro-2-picoline
5-Bromo-2-methyl-3-nitrop...
5-Bromo-2-methyl-3-nitropyridine
Pyridine,5-broMo-2-Methyl-3-nitro-
5-Bromo-2-methyl-3-nitropyridine >
5-Bromo-2-methyl-3-nitropyridine ISO 9001：2015 REACH | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C6H5BrN2O2 | [MDL Number]
MFCD09031419 | [MOL File]
911434-05-4.mol | [Molecular Weight]
217.02 |
| Chemical Properties | Back Directory | [Melting point ]
38.0 to 42.0 °C | [Boiling point ]
253 °C | [density ]
1.709 | [Fp ]
107 °C | [storage temp. ]
Room temperature. | [form ]
powder to crystal | [pka]
-0.44±0.20(Predicted) | [color ]
Light yellow to Amber to Dark green | [InChI]
InChI=1S/C6H5BrN2O2/c1-4-6(9(10)11)2-5(7)3-8-4/h2-3H,1H3 | [InChIKey]
FZZLWWNOYMHSIS-UHFFFAOYSA-N | [SMILES]
C1(C)=NC=C(Br)C=C1[N+]([O-])=O |
| Hazard Information | Back Directory | [Uses]
5-Bromo-2-methyl-3-nitropyridine is used as a reactant in the synthesis of MLN0905, a potent and orally bioavailable inhibitor of Polo-like kinase 1 (PLK1). | [Synthesis]
Step 2 - Synthesis of 5-bromo-2-methyl-3-nitropyridine
Diethyl 2-(5-bromo-3-nitropyridin-2-yl)malonate (1.2 g, 3.3 mmol) was dissolved in 7.0 N HCl (10 mL). The mixture was heated to reflux for 5 hours. After completion of the reaction, it was cooled to room temperature and extracted with dichloromethane: methanol (10:1, v/v). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography using petroleum ether: ethyl acetate (4:1, v/v) as eluent to afford 5-bromo-2-methyl-3-nitropyridine (0.7 g, yield: 89.7%).
1H-NMR (CDCl3, 400 MHz) δ 8.76 (s, 1H), 8.40 (s, 1H), 2.80 (s, 3H). | [References]
[1] Patent: US2008/194552, 2008, A1. Location in patent: Page/Page column 40
[2] Patent: WO2010/68292, 2010, A1. Location in patent: Page/Page column 78
[3] Patent: WO2013/33899, 2013, A1. Location in patent: Page/Page column 39
[4] Patent: WO2013/34048, 2013, A1. Location in patent: Page/Page column 46; 47
[5] Patent: WO2012/88411, 2012, A1. Location in patent: Page/Page column 64 |
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