3-substituted indolone derivative and preparation method and application thereof
A technology of derivatives and indolinones, which is applied in the field of 3-substituted indolinone derivatives and their preparation, can solve the problems of limited scope of application of substrates, low diastereoselectivity and enantioselectivity, and difficulty in obtaining Issues such as high diastereoselectivity and highly enantioselective products
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Embodiment 1
[0064]
[0065] Dissolve imine (0.1mmol), chiral phosphoric acid (0.01mmol) and rhodium acetate (0.002mmol) in 1mL of dichloromethane to form a reaction system, and dissolve diazo compound (0.2mmol) in 1mL of dichloromethane to form a solution , At -20°C, the solution of the diazo compound dissolved in dichloromethane was added dropwise to the reaction system within 1 hour using an autosampler pump. After the injection was completed, the reaction was continued to stir at -20°C for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, the structure of which was shown in formula (2-1). The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1-6:1) to obtain a pure product. Yield: 72%, dr: 99:1, ee 97%.
[0066] In this embodiment, R in the structural formula of the chiral phosphoric acid is a triphenylsilyl group.
[0067] 1 H NMR (CDCl 3 , 400MHz): δ (ppm) 7.25 (d, J = 7.5Hz, 1H), 7.19 (...
Embodiment 2
[0069]
[0070] Dissolve imine (0.1mmol), chiral phosphoric acid (0.01mmol) and rhodium acetate (0.002mmol) in 1mL of dichloromethane to form a reaction system, and dissolve diazo compound (0.2mmol) in 1mL of dichloromethane to form a solution , At -20°C, the solution of the diazo compound dissolved in dichloromethane was added dropwise to the reaction system within 1 hour using an autosampler pump. After the injection was completed, the reaction was continued to stir at -20°C for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, the structure of which was shown in formula (2-2). The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1-6:1) to obtain a pure product. Yield: 70%, dr: 99:1, ee 97%.
[0071] In this embodiment, R in the structural formula of the chiral phosphoric acid is a triphenylsilyl group.
[0072] 1 H NMR (CDCl 3 , 400MHz): δ (ppm) 7.23 (d, J = 7.1Hz, 1H), 7.19 (...
Embodiment 3
[0074]
[0075] Dissolve imine (0.1mmol), chiral phosphoric acid (0.01mmol) and rhodium acetate (0.002mmol) in 1mL of dichloromethane to form a reaction system, and dissolve diazo compound (0.2mmol) in 1mL of dichloromethane to form a solution , At -20°C, the solution of the diazo compound dissolved in dichloromethane was added dropwise to the reaction system within 1 hour using an autosampler pump. After the injection was completed, the reaction was continued to stir at -20°C for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product, the structure of which was shown in formula (2-3). The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1-6:1) to obtain a pure product. Yield: 57%, dr: 99:1, ee 95%.
[0076] In this embodiment, R in the structural formula of the chiral phosphoric acid is a triphenylsilyl group.
[0077] 1 H NMR (CDCl 3 , 400MHz): δ(ppm) 7.29-7.26(m, 2H), 7.19(t, J=7.6H...
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