Practical synthesis method of 3-acetyl-4-azaindole
A technique for the synthesis of azaindole, which is applied in the fields of medicine and chemical industry, can solve the problems of unavailable products, unsuitable for scale-up and industrial production, and low reaction yield, and achieve mild conditions, shorten the production process, and improve the reaction rate. The effect of temperature
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[0015] Example 1: Synthesis of 4-azaindole (Compound 2)
[0016]
[0017] 2-Methyl-3-nitropyridine (23.4g, 0.17mol), DMF-DMA (60g, 0.51mol) and DMF (100ml) were heated to 90°C and stirred for 8 hours. Cool to room temperature, pour the reaction solution into 300 ml of cold water, filter with suction to obtain a red solid, dissolve the solid in ethanol (500 ml), add 10% Pd / C (5 g), and stir at room temperature for 10 hours under a hydrogen atmosphere , Suction filtration (spread a layer of diatomaceous earth), wash with ethanol, and concentrate to obtain 18.1 g of brown solid 4-azaindole, yield: 90.5%.
[0018] EI-MS MS(m / z): 119.1(M + )
[0019] 1 H-NMR (DMSO-d6, 400MHz): δ8.29~8.27(m,1H), 7.76(d,1H), 7.61(d,1H), 7.08~7.04(m,1H), 6.54~6.52(m , 1H).
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[0020] Example 2: Synthesis of 3-acetyl-4-azaindole (Compound 3)
[0021]
[0022] 4-azaindole (21g, 0.18mol) was added to anhydrous aluminum trichloride (106.8g, 0.80mol), suspended in dichloroethane (800ml), heated to 50℃, stirred for 1 hour, and cooled to room temperature , Acetyl chloride (18.8g, 0.24mol) was added dropwise, after the addition, heated to 50°C and stirred for 2 hours, cooled, slowly added dropwise methanol (300ml) to quench the reaction, concentrated to dryness, added water (100ml), Sodium carbonate solution was added dropwise until a large amount of solids precipitated out, filtered with suction, the solids were washed with ethyl acetate (400 ml), the solids were discarded, the ethyl acetate layer was washed with saturated brine (50 ml), dried with anhydrous sodium sulfate, and filtered with suction , Concentrated to obtain a crude product, added n-hexane (60 ml), stirred, filtered with suction, and dried to obtain 20.2 g of off-white solid 3-acetyl-4-azaindo...
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