3-amino-3-hydroxymethyl oxoindole and 3-hydroxyl-3-hydroxymethyl oxoindole derivative, and preparation methods and applications thereof
A technology of indole derivatives and oxyindole, which is applied in the fields of drug combination, organic chemistry, and pharmaceutical formulations, can solve problems such as special structure, complicated operation, and harsh reaction conditions, and achieve high flexibility, simple and safe operation, and high efficiency. selective effect
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Embodiment 1
[0047]
[0048] Dissolve 2,6-dichloroaniline (0.1mmol), formaldehyde (0.6mmol) and rhodium acetate (0.001mmol) in 1mL of ethyl acetate to form a reaction system, keep the temperature at 60°C, and use an automatic injection pump to inject 1-benzyl A solution of 3-diazo-2-oxindole (0.10 mmol) dissolved in 1 mL of ethyl acetate was added to the reaction system within 1 hour. After the injection was completed, the reaction was continued to stir at 60° C. for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, the structure of which was Compound 1 shown above. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1-1:1) to obtain a pure product. Yield: 94%
[0049] 1 H NMR (400MHz, CDCl 3 )δ7.40-7.27 (m, 5H), 7.15 (td, 1H), 7.09 (d, 2H), 6.78 (dt, 3H), 6.69-6.59 (m, 1H), 5.27 (s, 1H), 5.04 (d, 1H), 4.82(d, 1H), 3.97(t, 1H), 3.87(dd, 1H), 3.15(dd, 1H);
[0050] 13 C NMR (100MHz, CDCl ...
Embodiment 2
[0052]
[0053] Dissolve aniline (0.10mmol), formaldehyde (0.60mmol) and rhodium acetate (0.001mmol) in 1mL ethyl acetate to form a reaction system, keep the temperature at 60°C, and use an autosampler pump to inject 1-benzyl-3-diazo - A solution of 2-oxindole (0.10 mmol) dissolved in 1 mL of ethyl acetate was added to the reaction system within 1 hour. After the injection was completed, the reaction was continued to stir at 60° C. for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, the compound 2 whose structure was shown above. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1-1:1) to obtain a pure product. Yield: 42%
[0054] 1 H NMR (400MHz, CDCl 3 )δ7.40-7.16(m, 8H), 7.06(t, 1H), 6.95(t, 2H), 6.84(d, 1H), 6.70(t, 1H), 6.27(d, 2H), 5.18(s , 1H), 5.11(d, 1H), 4.76(d, 1H), 3.92(t, 1H), 3.75-3.64(m, 1H), 3.12(d, 1H);
[0055] 13 C NMR (100MHz, CDCl 3 )δ 178.04, 145.5...
Embodiment 3
[0057]
[0058] Dissolve 4-chloroaniline (0.10mmol), formaldehyde (0.60mmol) and rhodium acetate (0.001mmol) in 1mL of ethyl acetate to form a reaction system, keep the temperature at 60°C, and use an automatic injection pump to inject 1-benzyl-3 - A solution of diazo-2-oxindole (0.10 mmol) dissolved in 1 mL of ethyl acetate was added to the reaction system within 1 hour. After the injection was completed, the reaction was continued to stir at 60° C. for 1 hour. The solvent was removed by rotary evaporation under reduced pressure to obtain the crude product, the structure of which was compound 3 shown above. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=10:1-1:1) to obtain a pure product. Yield: 89%
[0059] 1 H NMR (400MHz, CDCl 3 )δ7.60(dd, 4H), 7.26-7.22(m, 1H), 7.22-7.16(m, 2H), 7.06(t, 1H), 6.88(t, 2H), 6.84(d, 1H), 6.24 -6.12(m, 2H), 5.24(s, 1H), 5.09(d, 1H), 4.73(d, 1H), 3.97-3.82(m, 1H), 3.75-3.66(m, 1H), 3.46(d ,1H); ...
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