Preparation method of poly-substituted diphenylethylene indole derivative
A technology of stilbene derivatives and stilbene, which is applied in the field of preparation of stilbene stilbene derivatives, can solve problems such as long reaction time, and achieve short reaction time, high yield, and high environmental friendliness Effect
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Embodiment 1
[0021] Preparation of Distyrylindole Derivative 3aa
[0022]
[0023] Add N-methoxyindolecarboxamide 1a (0.1mmol, 19.0mg), 2a (0.1mmol, 17.8mg), dichlorobis(4-methylisopropylphenyl) into a 15ml thick-walled pressure-resistant tube Ruthenium(Ⅱ) (0.005mmol, 3.1mg) and sodium acetate (0.2mmol, 27.2mg) were added to water:dichloromethane (1.0mL, 9:1), stirred at room temperature, and reacted for 3 hours. After the reaction is complete, use a rotary evaporator to remove the solvent to obtain a crude product, which is separated by column chromatography (200-300 mesh silica gel) (petroleum ether / ethyl acetate=4 / 1), and uses a rotary evaporator to remove the solvent to obtain the target The yield of the unsubstituted distyrylindole derivative 3aa was 99%.
[0024] Spectrum analysis data 3aa:
[0025] 1 H NMR (400MHz, DMSO-d 6 )δ11.53(s,1H),10.44(s,1H),7.51(d,J=7.8Hz,1H),7.32(d,J=8.1Hz,1H),7.24(dd,J=5.0,1.7 Hz,3H),7.20–7.13(m,3H),7.09–7.02(m,5H),7.00–6.94(m,1H),6.68(d,J=1.5Hz,1...
Embodiment 2
[0027] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.
[0028]
[0029] Spectrum analysis data 3ba:
[0030] 1 H NMR (400MHz, DMSO-d 6 )δ11.57(s,1H),10.68(s,1H),7.73(d,J=1.7Hz,1H),7.29(d,J=8.6Hz,1H),7.24(dd,J=5.0,1.6 Hz,3H),7.18(d,J=1.9Hz,2H),7.16(d,J=3.0Hz,2H),7.09–7.02(m,4H),6.68(d,J=1.6Hz,1H), 3.42(s,3H). 13 C NMR (101MHz, DMSO-d 6 ( 24 h 19 BrN 2 NaO 2 + [M+Na] + 469.0528,found 469.0528.
Embodiment 3
[0032] Replace 1a in Example 1 with 1c, and other conditions are the same as Example 1. The experimental results are shown in Table 1.
[0033]
[0034] Spectrum analysis data 3ca:
[0035] 1 H NMR (400MHz, DMSO-d 6 )δ11.56(s,1H),10.67(s,1H),7.59(d,J=2.0Hz,1H),7.33(d,J=8.6Hz,1H),7.25(dd,J=5.0,1.7 Hz,3H),7.19(s,1H),7.16(d,J=2.6Hz,2H),7.05(ddt,J=7.4,3.3,1.7Hz,5H),6.68(d,J=1.5Hz,1H ),3.42(s,3H). 13 C NMR (101MHz, DMSO-d 6 ( 24 h 19 ClN 2 NaO 2 ++ [M+Na] + 425.1033, found 425.1028.
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