CN109305960B - Asymmetric N-pyridyl-2, 2-diindole compound and synthesis method thereof - Google Patents
Asymmetric N-pyridyl-2, 2-diindole compound and synthesis method thereof Download PDFInfo
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Abstract
The invention discloses an asymmetric N-pyridyl-2, 2-indole compound and a synthesis method thereof, which comprises the steps ofN-pyridylindole compound, indole compound, [ Cp ] Co (CO) I2]、AgSbF6HOPiv, Ag pivalate2O, NaOAc and organic solvent are mixed in the reaction tube and reacted in oil bath. The invention avoids the pre-functionalization of indole substrate in the traditional asymmetric indole compound synthesis method, thereby greatly improving the reaction efficiency and atom economy, and the obtained product has high yield, narrow melting point range and high purity, and the reaction does not need anhydrous and oxygen-free operation, and the operation is simple and feasible.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to an asymmetric N-pyridyl-2, 2-diindole compound and a synthesis method thereof.
Background
The 2, 2-diindole compound and the derivative thereof are important organic heterocycles and have important biological activity and certain medicinal value.
C.a. merlic et al (tetrahedron.2001, 57, 5199) report an asymmetric 2, 2-diindole compound, constructed primarily by a Pd-catalyzed coupling reaction, as shown in the following formula:
the main disadvantages of this method are: the selective pre-functionalization of indole substrates is difficult, and the synthesis of 2-iodoindole and 2-indolylboronic acid or 2-indoxyl tin-based compounds and zinc compounds is extremely difficult, requiring extremely harsh conditions and multi-step operations. Therefore, it is of great significance to develop a simple and efficient method for constructing the asymmetric diindole compound skeleton.
Disclosure of Invention
In order to overcome the defects, the invention aims to provide an asymmetric N-pyridyl-2, 2-diindole compound and a synthesis method thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
an asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
wherein R is1、R2Or R3Is H, alkyl, halogen, alkoxy or ester group.
The synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under the air atmosphere, N-pyridyl indole compound, [ Cp Co (CO) I2]、AgSbF6HOPiv, Ag pivalate2O, NaOAc and organic solvent are mixed in the reaction tube for oil bath reaction;
the structural general formula of the N-pyridyl indole compound is as follows:
the structural general formula of the indole compound is as follows:
wherein R is1、R2Or R3Is H, alkyl, halogen, alkoxy or ester group;
(2) and after the reaction is finished, cooling the reaction tube to room temperature, desalting the reaction mixture, washing, concentrating and purifying to obtain the target product N-pyridyl-2, 2-diindole compound.
Preferably, the N-pyridylindole compound, indole compound, Ag described in step (1)2O, NaOAc in a ratio of 0.2 mmol: 0.4-0.5 mmol: 0.4-0.44 mmol: 0.2-0.24mmol, [ Cp + Co (CO) I2]、AgSbF6The molar dosage of the HOPiv is 2.5-3.0%, 10-12% and 20-25% of the N-pyridyl indole compound respectively.
Preferably, the dosage ratio of the N-pyridyl indole compound to the organic solvent is as follows: 0.2 mmol: 1-3 mL.
Preferably, the oil bath reaction conditions are as follows: the temperature is 100 ℃ and 120 ℃, and the time is 10-15 h.
Preferably, the organic solvent is 1, 2-dichloroethane or toluene.
Preferably, step (2) is followed by the following steps:
(3) dissolving the N-pyridyl-2, 2-diindole compound obtained in the step (2) in dichloromethane, then dripping methyl trifluoromethanesulfonate MeOTf at the temperature of-2-1 ℃, stirring at room temperature for 6-10h, carrying out vacuum spin drying on the obtained mixture, adding Pd (OH)2C and ammonium formate, finally adding methanol, and stirring for 6-10h at 50-80 ℃;
(4) and after the reaction is finished, desalting the reaction mixture, washing, concentrating and purifying to obtain the 2, 2-diindole.
Preferably, the N-pyridyl-2, 2-diindole, the methyl trifluoromethanesulfonate MeOTf, Pd (OH) in the step (3)2The dosage ratio of ammonium formate to ammonium formate is as follows: 0.2 mmol: 0.22-0.26 mmol: 8-10 mg: 2-2.2 mmol.
Preferably, the dosage ratio of the N-pyridyl-2, 2-diindole, the dichloromethane and the methanol in the step (3) is 0.2 mmol: 2-3 mL: 2-3 mL.
The chemical reaction general formula is as follows:
wherein R is1、R2Or R3Is H, alkyl, halogen, alkoxy or ester group.
The invention has the following positive beneficial effects:
1. the invention provides a simple and efficient synthesis method of an asymmetric N-pyridyl-2, 2-diindole compound, which avoids the pre-functionalization of an indole substrate in the traditional synthesis method of the asymmetric diindole compound, thereby greatly improving the reaction efficiency and the atom economy, and the obtained target compound has high yield, narrow melting point range and high purity, and the reaction does not need anhydrous and anaerobic operation, and the operation is feasible and simple.
Detailed Description
The invention will be further illustrated with reference to some specific embodiments.
Example 1
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridyl indole compound, 0.4mmol of indole, [ Cp ] Co (CO) I2]0.005mmol、AgSbF6 0.02mmol、HOPiv 0.04mmol、Ag20.4mmol of O, 0.2mmol of NaOAc and 2ml of 1, 2-dichloroethane are mixed in a reaction tube and heated in an oil bath at 100 ℃ for 15 h;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction is finished, the reaction tube is cooled to room temperature, and the reaction mixture is subjected to desalting, washing, concentration and purification to obtain the target product N-pyridyl-2, 2-diindole compound with the yield of 86 percent and the melting point of 190-.1H NMR(400MHz,CDCl3)δ8.95(br,1H),8.73(d,J＝3.6Hz,1H),7.78(td,J＝7.8,1.7Hz,1H),7.71–7.64(m,1H),7.53(d,J＝7.8Hz,1H),7.48–7.41(m,1H),7.36(dd,J＝7.0,5.2Hz,1H),7.32(d,J＝8.1Hz,1H),7.27(d,J＝8.1Hz,1H),7.24–7.19(m,2H),7.17(t,J＝7.4Hz,1H),7.08(t,J＝7.4Hz,1H),6.94(s,1H),6.37(s,1H).13C NMR(101MHz,CDCl3)δ151.88,149.24,138.81,138.49,136.38,132.61,129.85,128.53,128.46,123.27,122.74,122.45,122.38,121.53,120.70,120.60,120.11,111.10,110.89,105.25,103.28；
(3) Dissolving 0.2mmol of the asymmetric N-pyridyl-2, 2-diindole compound obtained in the step (2) in 2mL of dichloromethane, then dropping 0.24mmol of methyl trifluoromethanesulfonate MeOTf at 0 ℃, stirring at room temperature for 6h, vacuum-drying the resulting mixture of the solvents, adding Pd (OH)2C8 mg and2mmol of ammonium formate, then adding 2ml of methanol, stirring for 6h at 60 ℃, desalting, washing, concentrating and purifying the reaction mixture to obtain the 2, 2-diindole, wherein the yield is 71 percent, 193-,1H NMR(400MHz,DMSO):δ11.54(br,1H),7.56(d,J＝8.5Hz,1H),7.40(d,J＝8.5Hz,1H),7.11(t,J＝8.1Hz,1H),7.02(d,J＝7.6Hz,1H),6.92(d,J＝0.2Hz,1H)；13C NMR(101MHz,DMSO):δ136.88,131.37,128.41,121.66,120.00,119.38,111.03,98.38。
the structural formula of the 2, 2-diindole is as follows:
example 2
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridylindole compound, 0.45mmol of 6-methylindole, and [ CpCo (CO) I2]0.006mol、AgSbF6 0.02mmol、HOPiv 0.05mmol、Ag20.4mmol of O, 0.22mmol of NaOAc and 3ml of toluene are mixed in a reaction tube and heated in oil bath at 110 ℃ for 11 h;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction is finished, the reaction tube is cooled to room temperature, and the reaction mixture is subjected to desalting, washing, concentration and purification to obtain the target product, wherein the yield is 72 percent, and the melting point is 194-196 ℃.1H NMR(400MHz,CDCl3)δ8.93(br,1H),8.68–8.58(m,1H),7.66(td,J＝7.8,1.9Hz,1H),7.59(dd,J＝6.3,2.6Hz,1H),7.45–7.37(m,1H),7.25(dd,J＝6.7,5.0Hz,1H),7.17–7.13(m,3H),7.06(d,J＝8.1Hz,1H),6.99(d,J＝8.0Hz,1H),6.84(s,1H),6.81(d,J＝7.0Hz,1H),6.34(d,J＝1.2Hz,1H),2.41(s,3H).13C NMR(101MHz,CDCl3)δ151.85,149.10,138.68,138.45,136.08,132.72,130.09,129.22,128.56,128.37,123.18,122.63,122.55,122.31,121.49,120.65,120.15,111.10,108.50,105.28,101.86,18.63。
Example 3
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridylindole compound, 0.5mmol of 5-chloroindole, and [ CpCo (CO) I2]0.0056mmol、AgSbF6 0.022mol、HOPiv 0.044mol、Ag2O0.42mmol, NaOAc 0.2mmol and toluene 2.2ml are mixed in a reaction tube and heated in oil bath at 110 ℃ for 13 h;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction is finished, the reaction tube is cooled to room temperature, and the reaction mixture is subjected to desalting, washing, concentration and purification to obtain the target product, wherein the yield is 82%, and the melting point is 180-.1H NMR(400MHz,DMSO)δ11.76(br,1H),8.71(d,J＝3.6Hz,1H),8.02(td,J＝7.7,1.8Hz,1H),7.72(dd,J＝5.4,3.2Hz,1H),7.58(dd,J＝6.9,5.1Hz,1H),7.46–7.40(m,2H),7.38(d,J＝8.6Hz,1H),7.30(dd,J＝5.8,2.8Hz,1H),7.24–7.12(m,3H),7.09(dd,J＝8.6,1.9Hz,1H),5.66(d,J＝1.1Hz,1H).13C NMR(101MHz,DMSO)δ151.42,150.05,139.61,139.14,135.41,132.53,131.71,129.62,128.21,124.39,124.09,123.65,123.00,122.28,121.68,121.12,119.66,113.06,111.32,104.59,101.01。
Example 4
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridylindole compound, 0.44mmol of 5-carbomethoxyindole, [ Cp ] Co (CO) I2]0.0052mmol、AgSbF6 0.024m mol、HOPiv 0.04mmol、Ag20.44mmol of O, 0.24mmol of NaOAc and 2.5ml of 1, 2-dichloroethane are mixed in a reaction tube and heated in oil bath at 120 ℃ for 12 h;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction is finished, cooling the reaction tube to room temperature, desalting, washing, concentrating and purifying the reaction mixture to obtain the target product, wherein the yield is 50%, and the melting point is 197-.1H NMR(400MHz,DMSO)δ11.95(br,1H),8.71(d,J＝3.6Hz,1H),8.07(s,1H),8.03(td,J＝7.8,1.8Hz,1H),7.77–7.70(m,2H),7.59(dd,J＝7.1,5.1Hz,1H),7.45(dd,J＝8.2,3.9Hz,2H),7.30(d,J＝6.8Hz,1H),7.24–7.17(m,3H),5.81(s,1H),3.82(s,3H).
13C NMR(101MHz,DMSO)δ167.51,151.37,150.07,139.63,139.53,139.17,132.38,131.86,128.19,128.12,124.13,123.71,123.31,123.13,123.02,121.69,121.43,121.16,111.52,111.32,104.67,102.49,52.08。
Example 5
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridylindole compound, 0.42mmol of 5-methoxyindole, and [ Cp Co (CO) I2]0.005mmol、AgSbF6 0.02mmol、HOPiv 0.042mmol、Ag20.42mmol of O, 0.22mmol of NaOAc and 2.4ml of toluene are mixed in a reaction tube and heated in oil bath at 120 ℃ for 10 h;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction is finished, the reaction tube is cooled to room temperature, and the reaction mixture is subjected to desalting, washing, concentration and purification to obtain the target product, wherein the yield is 76%, and the melting point is 200-.1H NMR(400MHz,CDCl3)δ8.84(s,1H),8.70(d,J＝3.7Hz,1H),7.76(t,J＝6.9Hz,1H),7.68–7.63(m,1H),7.46–7.39(m,1H),7.34(dd,J＝6.8,5.3Hz,1H),7.24–7.16(m,3H),6.96(s,1H),6.89(s,1H),6.81(dd,J＝8.7,2.1Hz,1H),6.27(s,1H),3.81(s,3H).
13C NMR(101MHz,CDCl3)δ154.47,151.90,149.20,138.77,138.48,132.67,131.64,130.49,128.89,128.55,123.22,122.71,122.37,121.52,120.67,112.92,111.62,111.09,105.08,103.05,102.18,55.84。
Example 6
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridyl indole compound, 0.46mmol of indole, [ Cp ] Co (CO) I2]0.005mmol、AgSbF6 0.02mol、HOPiv 0.04mmol、Ag20.4mmol of O, 0.2mmol of NaOAc and 2.6ml of 1, 2-dichloroethane are mixed in a reaction tube and heated in oil bath at 120 ℃ for 3 h;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction is finished, the reaction tube is cooled to room temperature, and the reaction mixture is subjected to desalting, washing, concentration and purification to obtain the target product, wherein the yield is 71 percent, and the melting point is 184-.1H NMR(400MHz,CDCl3)δ9.08(br,1H),8.72(d,J＝3.4Hz,1H),7.82(dd,J＝10.8,4.5Hz,1H),7.67(dd,J＝6.1,2.5Hz,1H),7.43(d,J＝7.1Hz,1H),7.41–7.36(m,1H),7.30(d,J＝7.9Hz,1H),7.22(dt,J＝8.1,7.1Hz,3H),7.16(dd,J＝9.5,2.0Hz,1H),6.98–6.78(m,2H),6.33(s,1H).13C NMR(101MHz,CDCl3):δ157.2,151.8,149.3,138.8,138.6,132.9,132.3,131.7,128.8(d,JC-F＝10.0Hz),128.5,123.4,122.9,122.4,121.6,120.8,111.5(d,JC-F＝9.0Hz),111.1,110.8(d,JC-F＝26.4Hz),105.6,105.2(d,JC-F＝23.7Hz),103.2,103.1。
Example 7
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridylindole compound, 0.5mmol of 5-methylindole, and [ CpCo (CO) I2]0.005mmol、AgSbF6 0.024mmol、HOPiv 0.04mmol、Ag2O0.42mmol, NaOAc 0.24mmol and toluene 3ml are mixed in a reaction tube and heated in oil bath at 110 ℃ for 5 h;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction, the reaction tube was cooled to room temperature, and the reaction mixture was desalted and washedWashing, concentrating and purifying to obtain the target product with the yield of 66 percent and the melting point of 190-.1H NMR(400MHz,DMSO)δ11.47(s,1H),8.72(d,J＝3.7Hz,1H),8.02(td,J＝7.8,1.7Hz,1H),7.78(d,J＝1.6Hz,1H),7.60(dd,J＝7.0,5.0Hz,1H),7.41(d,J＝7.9Hz,1H),7.27(d,J＝8.3Hz,2H),7.20–7.13(m,2H),7.10(s,1H),6.93(d,J＝8.1Hz,1H),5.55(s,1H),2.31(s,3H).13C NMR(101MHz,DMSO)δ151.21,150.08,139.68,137.49,135.44,134.79,129.54,129.36,128.63,128.45,126.04,124.34,124.30,123.13,123.11,120.21,120.04,112.79,111.38,103.12,101.43,21.53。
Example 8
An asymmetric N-pyridyl-2, 2-diindole compound, which has the chemical structural formula:
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under air atmosphere, 0.2mmol of N-pyridylindole compound, 0.42mmol of indole, [ Cp ] Co (CO) I2]0.006mmol、AgSbF6 0.022mmol、HOPiv 0.05mmol、Ag20.44mmol of O, 0.24mmol of NaOAc and 3ml of 1, 2-dichloroethane are mixed in a reaction tube and heated in oil bath at 120 ℃ for 12 hours;
the structural formula of the N-pyridyl indole compound is as follows:
(2) after the reaction is finished, the reaction tube is cooled to room temperature, and the reaction mixture is subjected to desalting, washing, concentration and purification to obtain the target product, wherein the yield is 52%, and the melting point is 193-.1H NMR(400MHz,DMSO)δ11.52(br,1H),7.89(t,J＝7.7Hz,1H),7.73–7.67(m,1H),7.44(d,J＝7.6Hz,1H),7.40–7.35(m,2H),7.30–7.25(m,1H),7.17(ddd,J＝10.2,6.4,5.1Hz,3H),7.12(s,1H),7.11–7.00(m,1H),6.98–6.92(m,1H),5.68(d,J＝1.8 Hz,1H),2.57(s,3H).13C NMR(101 MHz,DMSO)δ158.84,150.90,139.61,139.15,136.95,133.06,130.06,128.48,128.25,123.31,122.35,121.47,120.87,120.57,119.96,119.80,111.57,111.41,103.77,101.33,24.34。
Claims (7)
1. A synthetic method of an asymmetric N-pyridyl-2, 2-diindole compound is characterized in that the chemical structure general formula of the compound is as follows:
wherein R is1、R2Or R3Is H, alkyl, halogen, alkoxy or ester group;
the synthesis method of the asymmetric N-pyridyl-2, 2-diindole compound comprises the following steps:
(1) under the air atmosphere, N-pyridyl indole compound, [ Cp Co (CO) I2]、AgSbF6HOPiv, Ag pivalate2O, NaOAc and organic solvent are mixed in the reaction tube for oil bath reaction;
the structural general formula of the N-pyridyl indole compound is as follows:
the structural general formula of the indole compound is as follows:
wherein R is1、R2Or R3Is H, alkyl, halogen, alkoxy or ester group;
(2) after the reaction is finished, cooling the reaction tube to room temperature, desalting the reaction mixture, washing, concentrating and purifying to obtain a target product N-pyridyl-2, 2-diindole compound;
n-pyridylindolation as described in step (1)Compound, indole compound, Ag2O, NaOAc in a ratio of 0.2 mmol: 0.4-0.5 mmol: 0.4-0.44 mmol: 0.2-0.24mmol, [ Cp + Co (CO) I2]、AgSbF6The molar dosage of the HOPiv is 2.5-3.0%, 10-12% and 20-25% of the N-pyridyl indole compound respectively.
2. The method for synthesizing an asymmetric N-pyridyl-2, 2-diindole compound according to claim 1, wherein the amount ratio of the N-pyridyl indole compound to the organic solvent is: 0.2 mmol: 1-3 mL.
3. The process for the synthesis of an asymmetric N-pyridyl-2, 2-diindole compound according to claim 1, wherein the oil bath reaction conditions are: the temperature is 100 ℃ and 120 ℃, and the time is 10-15 h.
4. The method for synthesizing an asymmetric N-pyridyl-2, 2-diindole compound according to claim 1, wherein the organic solvent is 1, 2-dichloroethane or toluene.
5. The method of synthesizing an asymmetric N-pyridyl-2, 2-diindole compound according to claim 1, wherein the step (2) is further followed by the steps of:
(3) dissolving the N-pyridyl-2, 2-diindole compound obtained in the step (2) in dichloromethane, then dripping methyl trifluoromethanesulfonate MeOTf at the temperature of-2-1 ℃, stirring at room temperature for 6-10h, carrying out vacuum spin drying on the obtained mixture, adding Pd (OH)2C and ammonium formate, finally adding methanol, and stirring for 6-10h at 50-80 ℃;
(4) and after the reaction is finished, desalting the reaction mixture, washing, concentrating and purifying to obtain the 2, 2-diindole.
6. The method for synthesizing an asymmetric N-pyridyl-2, 2-diindole compound according to claim 5, wherein the N-pyridyl-2, 2-diindole in the step (3), methyl trifluoromethanesulfonate MeOTf, Pd (OH)2C, ammonium formateThe dosage ratio is as follows: 0.2 mmol: 0.22-0.26 mmol: 8-10 mg: 2-2.2 mmol.
7. The method for synthesizing an asymmetric N-pyridyl-2, 2-diindole compound according to claim 5, wherein the ratio of the dosage of N-pyridyl-2, 2-diindole, dichloromethane and methanol in step (3) is 0.2 mmol: 2-3 mL: 2-3 mL.
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| 三氟甲磺酸催化的2,3-二吲哚衍生物的合成;章吕烨等;《有机化学》;20180514;第38卷;第2028-2035页 * |
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