New method for preparing 1-(6-methylpyridine-3-yl)-2-[4-(methylsulfanyl)phenyl]acetone
A technology of methylsulfanyl and methylpyridine, which is applied in the field of preparation of intermediates, can solve the problems of falling off, easy explosion of the reaction system, etc., and achieves the effect of reducing the danger of easy explosion and avoiding the easy decomposition of heat to generate gas.
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Embodiment 1
[0051] Synthesis of isoxazolidin-2-yl-(6-methylpyridin-3-yl)-methanone of formula (III)
[0052] synthetic route:
[0053]
[0054] Under nitrogen protection, 150 g of 6-methylnicotinic acid methyl ester (V) and 120 g of isoxazole hydrochloride (IV) were added to 500 ml of toluene, and the solution was cooled to -20°C. Slowly add 2.2 mol / L tetrahydrofuran solution of isopropylmagnesium chloride into the cooled solution. Reaction temperature is controlled between-20 ℃ to-10 ℃, after stirring for 0.5 hour, add 500ml20% acetic acid solution, separate and remove water phase, evaporate organic solvent under reduced pressure, obtain the formula (III) compound of yellow liquid (152g , 80%).1 H NMR (300MHz, CDCl 3 )δ2.36(t, 2H, J=7.8Hz), 2.59(s, 3H), 3.94(m, 4H), 7.19(d, 1H, J=8.1Hz), 8.01(dd, 1H, J=7.8 Hz, 1.2Hz), 8.94 (s, 1H).
[0055] Synthesis of 1-(6-methylpyridin-3-yl)-2-[4-(methylsulfanyl)phenyl]ethanone of formula (I)
[0056] synthetic route:
[0057]
[0058] Und...
Embodiment 2
[0060] Synthesis of isoxazolidin-2-yl-(6-methylpyridin-3-yl)-methanone of formula (III)
[0061] synthetic route:
[0062]
[0063] Add 230g of sodium carbonate to 600ml of water and cool to 15°C. 120 g of isoxazole hydrochloride (IV) was added thereto. 155 g of 6-methylnicotinoyl chloride (VI) was evenly suspended and dispersed in dichloromethane, and then added to 1% aqueous sodium carbonate solution at 25°C. The mixed solution was stirred for 0.5 hour, the aqueous phase was separated and removed, and the organic phase was washed with water and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure to obtain the compound of formula (III) (123 g, 65%) as a yellow liquid.
[0064] Synthesis of 1-(6-methylpyridin-3-yl)-2-[4-(methylsulfanyl)phenyl]ethanone of formula (I)
[0065] synthetic route:
[0066]
[0067] Under nitrogen protection, 191 g of isoxazolidin-2-yl-(6-methylpyridin-3-yl)-methanone (III) was dissolved in 350 ml...
Embodiment 3
[0069] A kind of new method for preparing 1-(6-methylpyridin-3-yl)-2-[4-(methylsulfanyl)phenyl]ethanone, will comprise the Grignard reagent of formula (II) and formula (III) Isoxazolidin-2-yl-(6-methylpyridin-3-yl)-methanone is prepared by reacting in the solvent toluene at a molar ratio of 1:1 between -10°C and 0°C product;
[0070] The structural formula of described Grignard reagent is:
[0071]
[0072] Wherein X is a chlorine atom;
[0073] Described isoxazolidin-2-yl-(6-methylpyridin-3-yl)-methanone: it is to comprise the isoxazole salt of formula (IV) and the 6-methyl smoke of formula (V) Methyl acid is prepared by reacting in the solvent toluene in the presence of sodium hydroxide at a molar ratio of 1.5:1.
[0074] The molecular formula of described isoxazole salt is:
[0075]
[0076] Wherein Y is hydrochloric acid.
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