3,3-disubstituted oxoindole and preparation method thereof
A technology of oxindole and disubstitution, applied in chemical instruments and methods, organic chemistry, chemical/physical processes, etc., can solve the problems of high atom economy, explosive hydrogen, lack of reaction, etc., and achieve high reaction yield, High safety and reduced reaction cost
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Embodiment 1
[0022]
[0023] Under nitrogen protection, palladium chloride (1.7 mg, 0.01 mmol, 5 mol%) and sodium hydride (60% in oil, 16 mg, 0.4 mmol, 2 equiv) were suspended in DMA (1.0 mL), stirred at room temperature for 5 minutes, and added A solution of compound 1a (0.2 mmol) in DMA (0.5 mL) was reacted at room temperature for 30 minutes. After the reaction of the raw materials was completed, benzyl bromide (1.5 eq.) was added, and the reaction was continued with stirring. After the raw materials are reacted, the reaction is quenched by adding saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase is collected, the solvent is spin-dried to obtain the crude product, and the column chromatography finally obtains compound 3a with a yield of 98%. 1 H NMR (400 MHz, CDCl 3 ):δ 7.38-7.27 (m, 4H), 7.13-7.04 (m, 7H), 7.02-6.94 (m, 5H), 6.64 (d, J = 7.3Hz, 2H), 6.21 (d, J = 7.7 Hz, 1H), 3.47 (d, J = 12.9 Hz, 2H), 3.25 (d, J =12.9 Hz, 2H). 13 C NMR (151 ...
Embodiment 2
[0025]
[0026] Under nitrogen protection, palladium chloride (1.7 mg, 0.01 mmol, 5 mol%) and sodium hydride (60% in oil, 16 mg, 0.4 mmol, 2 equiv) were suspended in DMA (1.0 mL), stirred at room temperature for 5 minutes, and added A solution of compound 1a (0.2 mmol) in DMA (0.5 mL) was reacted at room temperature for 30 minutes. After the reaction of the raw materials was completed, methyl iodide (2.5 eq.) was added, and the reaction was continued with stirring. After the raw materials are reacted, the reaction is quenched by adding saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase is collected, and the solvent is spin-dried to obtain the crude product. The column chromatography finally obtains compound 3b with a yield of 98%. 1 H NMR (400 MHz, Chloroform- d ): δ 7.41 (t, J = 7.5 Hz, 2H), 7.37-7.28 (m, 2H), 7.15-7.02 (m,5H), 6.94 (d, J = 7.6 Hz, 2H), 6.86 (d, J = 7.1 Hz, 2H), 6.55-6.45 (m, 1H), 3.27 (d, J = 12.8 Hz, 1H), 3.09 (d,...
Embodiment 3
[0028]
[0029] Under nitrogen protection, palladium chloride (1.7 mg, 0.01 mmol, 5 mol%) and sodium hydride (60% in oil, 16 mg, 0.4 mmol, 2 equiv) were suspended in DMA (1.0 mL), stirred at room temperature for 5 minutes, and added A solution of compound 1a (0.2 mmol) in DMA (0.5 mL) was reacted at room temperature for 30 minutes. After the reaction of the raw materials was complete, methyl acrylate (6 eq.) was added, and the reaction was continued with stirring. After the raw materials are reacted, the reaction is quenched by adding saturated aqueous ammonium chloride solution, extracted with ethyl acetate, the organic phase is collected, and the solvent is spin-dried to obtain the crude product. The column chromatography finally obtains compound 3c with a yield of 97%. 1 H NMR (400 MHz, CDCl 3 ): δ 7.45-7.28 (m, 4H), 7.15-7.01 (m, 5H), 6.91 (d, J = 7.4 Hz, 2H), 6.84 (d, J = 7.1 Hz, 2H), 6.51-6.42 (m, 1H), 3.56 (s, 3H), 3.29 (d, J = 12.8Hz, 1H), 3.11 (d, J = 12.7 Hz, 1H), 2...
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