Pyridine, 3-bromo-6-methoxy-2,4-dimethyl- (9CI) synthesis
- Product Name:Pyridine, 3-bromo-6-methoxy-2,4-dimethyl- (9CI)
- CAS Number:819069-57-3
- Molecular formula:C8H10BrNO
- Molecular Weight:216.08
89694-55-3
74-88-4
819069-57-3
Step 2: Synthesis of 3-bromo-6-methoxy-2,4-dimethylpyridine In a 500 mL three-necked round-bottomed flask, nitrogen displacement was performed and an inert atmosphere was maintained. To the flask was added 5-bromo-4,6-dimethylpyridin-2(1H)-one (3.90 g, 19.30 mmol, 1.00 eq.), dichloromethane (150 mL) and silver carbonate (Ag2CO3, 7.34 g, 0.0266 mol, 1.40 eq.). Iodomethane (Mel, 28.4 g, 0.2 mol, 10.50 eq.) was slowly added to the mixture with stirring. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solid was collected by filtration and the filter cake was washed with dichloromethane (50 mL). The combined filtrates were concentrated under reduced pressure to give 3.91 g (94% yield) of 3-bromo-6-methoxy-2,4-dimethylpyridine as a brown oil. Mass Spectrometry (ESI) m/z measured value: C8H10BrNO [M + H]+: 216.
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Yield:819069-57-3 94%
Reaction Conditions:
in methanol at 100; for 2 h;
Steps:
87.1 Step 1: Synthesis of 3-bromo-6-methoxy-2,4-dimethyl-pyridine
A mixture of 3-bromo-6-chloro-2,4-dimethyl-pyridine (900 mg, 4.08 mmol) and sodium methanolate in methanol (9.0 mL, 30% w/w in methanol) was stirred at 100 °C for 2 hours. After cooling to room temperature, the reaction mixture was quenched with water and extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a light yellow oil. Yield: 830 mg, 94%. LCMS (ESI) m/z: 215.9 (M+H).
References:
WO2022/109492,2022,A1 Location in patent:Page/Page column 379
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