| Identification | Back Directory | [Name]
3-BROMO-2-CHLORO-6-METHOXYPYRIDINE | [CAS]
777931-67-6 | [Synonyms]
EOS-61428
Pyridine, 3-bromo-2-chloro-6-methoxy- | [Molecular Formula]
C6H5BrClNO | [MDL Number]
MFCD10699710 | [MOL File]
777931-67-6.mol | [Molecular Weight]
222.47 |
| Chemical Properties | Back Directory | [Boiling point ]
243.8±35.0 °C(Predicted) | [density ]
1.650±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [pka]
-0.37±0.10(Predicted) | [Appearance]
White to off-white Solid |
| Questions And Answer | Back Directory | [Uses]
2-Chloro-6-methoxy-3-bromopyridine can be used as a pharmaceutical synthesis intermediate. | [Application]
2-Chloro-6-methoxy-3-bromopyridine can be used as a pharmaceutical synthesis intermediate, such as in the preparation of 2-(6-(1-ethyl-4-fluoro-1H-indazol-6-yl)-2-methoxypyridin-3-yl)-3-methylbutanal: In a 100 mL vial maintained under an inert nitrogen atmosphere, 2-chloro-6-methoxy-3-bromopyridine (2.00 g, 8.900 mmol, 1.00 equivalent) was added, along with Pd(dppf)Cl2.CH2Cl2 (0.36 g, 0.450 mmol, 0.05 equivalent) and Zn(CH3)2 (17 mL, 17.000 mmol, 2.00 equivalent) were added to a solution in 20 mL of 1,4-dioxane. The resulting solution was stirred at 90 °C for 16 h. The mixture was then concentrated under vacuum. The residue was purified by silica gel chromatography and further purified with ethyl acetate/petroleum ether (2:98) to give 2-(6-(1-ethyl-4-fluoro-1H-indazole-6-yl)-2-methoxypyridin-3-yl)-3-methylbutanal as a yellow oil. |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 2-chloro-3-bromo-6-methoxypyridine from 2-chloro-6-methoxypyridine: To a stirred solution of 2-chloro-6-methoxypyridine (7.00 g, 48.8 mmol) in acetonitrile (25 mL) was added N-bromosuccinimide (NBS, 13.0 g, 73.1 mmol) at room temperature. The reaction mixture was refluxed for 24 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium thiosulfate (Na2S2O3) and extracted with ethyl acetate (EtOAc). The organic layer was dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, hexane-ethyl acetate = 98:2) afforded 2-chloro-3-bromo-6-methoxypyridine (6.83 g, 63% yield) as a colorless solid. The product was characterized by the following data: melting point 64-65 °C; IR spectra (film, cm-1 ): 1584, 1551, 1466, 1408, 1344, 1306, 1256, 1155, 1121, 1022, 1009; 1H-NMR (CDCl3, 500 MHz) δ: 7.72 (d, J = 8.50 Hz, 1H), and 6.58 (d, J = 8.50 Hz, 1H), 3.92 (s, 3H); 13C-NMR (CDCl3, 125 MHz) δ: 162.4, 147.3, 143.8, 110.9, 110.1, 54.3; High-resolution mass spectrometry (ESI-TOF): the calculated value C6H6BrClNO [(M + H)+ ] was 221.9316, and the measured value was 221.9314. | [References]
[1] MedChemComm, 2017, vol. 8, # 4, p. 796 - 806
[2] Organic Letters, 2014, vol. 16, # 7, p. 1980 - 1983
[3] Chemical and Pharmaceutical Bulletin, 2016, vol. 64, # 7, p. 723 - 732 |
|
|