3,3'-disubstituted-3-hydroxy bis-indolinone derivative and preparation method and application thereof
A kind of technology of hydroxybisindolone and derivatives, applied in 3 fields
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Embodiment 1
[0044]
[0045]Dissolve N-benzyl isatin (0.12 mmol) and rhodium acetate (0.0012 mmol) in 1 mL of tetrahydrofuran to form a reaction system, and dissolve N-methyldiazoacetanilide (0.24 mmol) in 1 mL of tetrahydrofuran to form a solution. A solution of N-methyldiazoacetanilide dissolved in tetrahydrofuran was added dropwise to the reaction system within 1 hour using an automatic injection pump. After the sample injection, continue to stir at room temperature for 0.5 hours. The solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, the structure of which was shown in formula (1-1). The crude product was purified by column chromatography (petroleum ether:ethyl acetate=15:1-4:1) to obtain a pure product. Yield: 66%, dr value: 92:8.
[0046] 1 H-NMR (CDCl 3 , 500MHz): δ 7.58 (d, J = 7.2 Hz, 1 H), 7.20-7.30 (m, 2 H), 7.10-7.18 (m, 2 H), 7.07-7.08 (m, 2 H), 6.88 (d, J = 7.8 Hz, 1 H), 6.70 (t, J = 9.2 Hz, 1 H), 6.57-6.69 (m, 3 H), 6.2...
Embodiment 2
[0049]
[0050] Dissolve N-benzyl isatin (0.12 mmol) and rhodium acetate (0.0012 mmol) in 1 mL of toluene to form a reaction system, and dissolve N-methyldiazoacetanilide (0.24 mmol) in 1 mL of toluene to form a solution. A solution of N-methyldiazoacetanilide dissolved in toluene was added dropwise to the reaction system within 1 hour using an auto-sampling pump. After the sample injection, continue to stir at room temperature for 0.5 hours. The solvent was removed by rotary evaporation under reduced pressure to obtain a crude product whose structure is shown in formula (1-2). The crude product was purified by column chromatography (petroleum ether:ethyl acetate=15:1-4:1) to obtain a pure product. Yield: 60%, dr value: 90:10.
Embodiment 3
[0052]
[0053] Dissolve N-benzyl isatin (0.12 mmol) and rhodium acetate (0.0012 mmol) in 1 mL of dichloromethane to form a reaction system, and dissolve N-methyldiazoacetanilide (0.24 mmol) in 1 mL of dichloromethane to form a reaction system Solution, at room temperature, the solution of N-methyldiazoacetanilide dissolved in dichloromethane was added dropwise to the reaction system within 1 hour with an automatic injection pump. After the injection was completed, stirring was continued at room temperature for 0.5 hours. The solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, the structure of which was shown in formula (1-3). The crude product was purified by column chromatography (petroleum ether:ethyl acetate=15:1-4:1) to obtain a pure product. Yield: 68%, dr value: 80:20.
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