CN112724065A - Synthetic method of 2-fluoroindole compound - Google Patents
Synthetic method of 2-fluoroindole compound Download PDFInfo
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
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Abstract
The invention discloses a synthetic method of a 2-fluoroindole compound, which comprises the following steps: (1) adding an o-aminochalcone compound, bromodifluoroacetic acid ethyl ester, alkali and an organic solvent into a pressure-resistant sealed reaction vessel, and stirring and reacting for 10-15h at 50-100 ℃ in a nitrogen atmosphere; (2) cooling the material obtained in the step (1) to room temperature, adding ethyl acetate, fully mixing, and sequentially filtering and washing with ethyl acetate to obtain an organic phase; (3) and (3) carrying out spin drying on the organic solvent in the organic phase obtained in the step (2), and then carrying out purification and elution by an eluent to obtain the 2-fluoroindole compound. The method can efficiently realize the synthesis of the 2-fluoroindole compound by taking the o-amino chalcone compound as a raw material under mild conditions and adding alkali and a solvent in the presence of nitrogen.
Description
Technical Field
The invention belongs to the technical field of organic materials, and particularly relates to a synthetic method of a 2-fluoroindole compound.
Background
The fluorine atom or the fluorine-containing group has unique physicochemical properties such as acid-base property, lipid solubility, metabolic stability and the like. In addition, the fluorine-containing compound can also control reactivity and stereochemistry in the asymmetric reaction. The introduction of fluorine atoms into bioactive scaffold materials has become increasingly appreciated in the organic and pharmaceutical chemistry fields over the last decade.
Indole is a very important heterocyclic skeleton and is widely present in natural products, bioactive compounds and other functional molecules.
In the prior art, 2-fluoroindole compounds are difficult to synthesize and few in the existing synthesis method, and the 2-fluoroindole compounds are mainly synthesized by synthesizing indole compounds, and then fluorinating the indole compounds, or by activating indole rings by transition metals such as palladium, copper, silver, ruthenium and the like through C-H activation. These methods are troublesome, have harsh reaction conditions, require the use of transition metals and the like, and have high synthesis cost values, thereby severely limiting the application thereof. How to realize the high-efficiency synthesis of the 2-fluoroindole compounds becomes the key and difficult point of the current research.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a synthetic method of a 2-fluoroindole compound.
The technical scheme of the invention is as follows:
a synthetic method of 2-fluoroindole compounds comprises the following steps:
(1) adding an o-aminochalcone compound, bromodifluoroacetic acid ethyl ester, alkali and an organic solvent into a pressure-resistant sealed reaction vessel, and stirring and reacting for 10-15h at 50-100 ℃ in a nitrogen atmosphere; the structural formula of the o-amino chalcone compound is one of the following formulas:
(2) cooling the material obtained in the step (1) to room temperature, adding ethyl acetate, fully mixing, and sequentially filtering and washing with ethyl acetate to obtain an organic phase;
(3) and (3) carrying out spin drying on the organic solvent in the organic phase obtained in the step (2), and then carrying out purification and elution by an eluent to obtain the 2-fluoroindole compound.
In a preferred embodiment of the invention, the base is potassium phosphate, potassium carbonate, potassium hydroxide, cesium carbonate, sodium carbonate or sodium hydroxide.
Further preferably, the base is potassium phosphate.
In a preferred embodiment of the present invention, the organic solvent is acetonitrile, 1, 4-dioxane, acetone or tetrahydrofuran.
Further preferably, the organic solvent is acetonitrile.
In a preferred embodiment of the invention, the eluent consists of petroleum ether and dichloromethane.
Further preferably, the volume ratio of the petroleum ether to the dichloromethane is 1-5: 1.
More preferably, the volume ratio of the petroleum ether to the dichloromethane is 5: 1
In a preferred embodiment of the invention, the ratio of the o-aminochalcone compound, ethyl bromodifluoroacetate, the base and the organic solvent is 0.1-0.3 mmol: 0.5-1 mmol: 1.5-2.5 mL.
More preferably, the proportion of the o-aminochalcone compound, the ethyl bromodifluoroacetate, the base and the organic solvent is 0.2 mmol: 0.6 mmol: 2 mL.
The invention has the beneficial effects that:
1. the method can efficiently realize the synthesis of the 2-fluoroindole compound by taking the o-amino chalcone compound as a raw material under mild conditions and adding alkali and a solvent in the presence of nitrogen.
2. In the prior art, transition metals such as palladium, copper, silver, ruthenium and the like are mostly needed for synthesizing the 2-fluoroindole compounds, the synthesis cost is high, green chemistry is not realized, and the synthesis method disclosed by the invention does not use the transition metals, has the characteristic of environmental friendliness and accords with the concept of green chemistry.
3. In the prior art, indole substrates need to be synthesized in advance for synthesizing the 2-fluoroindole compounds, so that the problems of poor substrate compatibility and the like are caused.
Detailed Description
The technical solution of the present invention is further illustrated and described by the following detailed description.
Example 1
The reaction formula of this example is as follows:
(1) adding 0.2mmol of o-dimethylaminochalcone, 0.6mmol of ethyl bromodifluoroacetate and 0.6mmol of potassium phosphate into a pressure-resistant sealed reaction tube, removing air, introducing nitrogen, injecting 2mL of acetonitrile into the pressure-resistant sealed reaction tube, stirring and reacting for 12 hours at 90 ℃, and tracking by TLC and GC in the reaction process to determine specific reaction time;
(2) taking the material obtained in the step (1) out of the pressure-resistant sealed reaction tube, cooling to room temperature, adding ethyl acetate, fully mixing, filtering and washing with ethyl acetate in sequence, and combining to obtain an organic phase;
(3) and (3) carrying out spin drying on acetonitrile in the organic phase obtained in the step (2), purifying by using a silica gel column, and eluting by using an eluent (petroleum ether: dichloromethane is 5: 1) to obtain the 2-fluoromethyl-3-acetophenone azomethylindole, wherein the yield is 83%.
The nuclear magnetic data are as follows:
1H NMR(500MHz,Chloroform-d)68.15-8.08(m,2H),7.61-7.54(m,2H),7.49(dd,J=8.4,7.0Hz,2H),7.25-7.16(m,3H),4.35(s,2H),3.61(s,3H).
13C NMR(126MHz,Chloroform-d)δ196.70,196.69,151.11,136.41,133.16,130.64,128.68,128.55,125.50,121.29,121.26,120.47,118.91,118.86,108.91,108.90,84.12,84.03,32.91,32.88,27.94,27.93.
19F NMR(471MHz,Chloroform-d)δ-138.82.
example 2
The reaction formula of this example is as follows:
(1) adding 0.2mmol of o-dimethylaminonaphthyl chalcone, 0.6mmol of bromodifluoroacetic acid ethyl ester and 0.6mmol of potassium phosphate into a pressure-resistant sealed reaction tube, removing air, introducing nitrogen, injecting 2mL of acetonitrile into the pressure-resistant sealed reaction tube, stirring and reacting for 12 hours at 90 ℃, and tracking by TLC and GC in the reaction process to determine specific reaction time;
(2) taking the material obtained in the step (1) out of the pressure-resistant sealed reaction tube, cooling to room temperature, adding ethyl acetate, fully mixing, filtering and washing with ethyl acetate in sequence, and combining to obtain an organic phase;
(3) and (3) carrying out spin drying on acetonitrile in the organic phase obtained in the step (2), purifying by using a silica gel column, and eluting by using an eluent (petroleum ether: dichloromethane is 5: 1) to obtain the 2-fluoromethyl-3-acetophenone azomethyl naphthyl indole with the yield of 91%.
Nuclear magnetic data:
1H NMR(500MHz,Chloroform-d)δ8.65(s,1H),8.12(dt,J=8.5,2.1Hz,1H),7.98(d,J=8.0Hz,1H),7.88(dd,J=10.0,8.1Hz,2H),7.63-7.53(m,3H),7.24-7.14(m,3H),4.45(s,2H),3.62(d,J=1.9Hz,3H).
13C NMR(126MHz,Chloroform-d)δ196.67,151.10,148.99,135.62,133.68,132.57,130.62,130.24,129.68,128.50,128.47,127.79,126.76,124.29,121.28,121.26,120.47,118.92,118.87,108.87,84.25,84.16,33.01,32.99,27.97,27.95.
19F NMR(471MHz,Chloroform-d)δ-138.77.
example 3
The substrate of the present invention was investigated for universality and good functional group compatibility under the same reaction conditions as in example 1 and example 2, and the o-dimethylamino chalcone and the o-dimethylamino naphthyl chalcone in the above examples were replaced as follows:
the corresponding products obtained were as follows:
the nuclear magnetic data of the above products are specifically as follows:
1528
1H NMR(500MHz,Chloroform-d)δ8.15(d,J=8.5Hz,2H),7.69(d,J=8.5Hz,2H),7.65-7.61(m,2H),7.53(d,J=7.8Hz,1H),7.48(t,J=7.5Hz,2H),7.43-7.39(m,1H),7.23-7.19(m,2H),7.16(dt,J=8.1,4.1Hz,1H),4.35(s,2H),3.64(s,3H).
13C NMR(126MHz,Chloroform-d)δ196.28,145.76,139.91,135.06,130.62,129.13,128.97,128.24,127.28,127.27,121.27,121.24,120.46,118.90,118.85,108.85,32.99,32.96,27.98.
19F NMR(471MHz,Chloroform-d)δ-138.82.
1276
1H NMR(500MHz,Chloroform-d)δ7.81(d,J=8.4Hz,2H),7.76(d,J=8.6Hz,2H),7.50(d,J=7.7Hz,1H),7.22(q,J=7.6Hz,2H),7.19-7.14(m,1H),4.26(s,2H),3.62(s,3H).
13C NMR(126MHz,Chloroform-d)δ195.98,148.90,137.94,135.57,130.61,129.94,125.25,121.40,121.37,120.56,118.80,118.75,108.95,108.94,101.11,83.79,83.71,32.91,32.89,28.00,27.99.
19F NMR(471MHz,Chloroform-d)δ-138.62.
1464
1H NMR(500MHz,Chloroform-d)δ7.98(d,J=8.6Hz,2H),7.51(dd,J=7.8,1.1Hz,1H),7.26(d,J=2.4Hz,1H),7.25(s,1H),7.20(dd,J=3.7,1.1Hz,2H),7.14(ddd,J=8.1,4.9,3.4Hz,1H),4.27(s,2H),3.62(s,3H),2.50(s,3H).
13C NMR(126MHz,Chloroform-d)δ195.75,145.90,132.62,130.59,128.94,125.41,125.36,125.01,121.26,121.23,120.44,118.90,118.85,108.84,108.83,84.23,84.15,32.77,32.75,27.97,27.95,14.75.
19F NMR(471MHz,Chloroform-d)δ-138.89.
1770
1H NMR(500MHz,Chloroform-d)δ8.12(d,J=8.5Hz,2H),7.75(d,J=8.4Hz,2H),7.48-7.45(m,1H),7.21(d,J=4.0Hz,2H),7.15(dt,J=8.1,4.1Hz,1H),4.31(s,2H),3.64(s,3H).
13C NMR(126MHz,Chloroform-d)δ195.27,139.27,132.49,130.60,128.89,125.01,121.54,121.51,120.67,118.61,118.56,117.94,116.33,108.99,83.15,33.32,33.29,28.02.
19F NMR(471MHz,Chloroform-d)δ-138.50.
1508
1H NMR(500MHz,Chloroform-d)δ7.84(dd,J=7.7,1.4Hz,1H),7.48(dd,J=7.8,1.1Hz,1H),7.37(td,J=7.4,1.4Hz,1H),7.29(td,J=7.6,1.3Hz,1H),7.24(d,J=7.7Hz,1H),7.22-7.19(m,2H),7.16(ddd,J=8.1,5.4,2.9Hz,1H),4.27(s,2H),3.62(s,3H),2.49(s,3H).
13C NMR(126MHz,Chloroform-d)δ200.67,138.61,137.30,131.93,131.22,130.50,128.49,125.53,125.44,121.12,121.09,120.30,118.61,118.56,108.77,108.76,84.13,84.05,35.48,35.46,27.85,27.83,21.23.
19F NMR(471MHz,Chloroform-d)δ-139.15.
1631
1H NMR(500MHz,Chloroform-d)δ7.91(d,J=1.8Hz,1H),7.87(dd,J=7.9,2.0Hz,1H),7.55(d,J=7.8Hz,1H),7.25(d,J=7.9Hz,1H),7.24-7.21(m,2H),7.18(ddd,J=8.1,5.9,2.4Hz,1H),4.33(s,2H),3.64(s,3H),2.35(d,J=2.8Hz,6H).
13C NMR(126MHz,Chlotoform-d)δ196.59,142.65,136.96,134.31,130.61,129.84,129.70,126.28,125.49,121.19,121.16,120.38,118.95,118.90,108.80,108.78,84.41,32.79,32.77,27.92,27.90,20.03,19.81.
19F NMR(471MHz,Chloroform-d)δ-139.02.
1509
1H NMR(500MHz,Chloroform-d)δ8.18(dd,J=2.9,1.3Hz,1H),7.61(dd,J=5.1,1.3Hz,1H),7.54(dd,J=7.8,1.1Hz,1H),7.30(dd,J=5.1,2.9Hz,1H),7.23-7.19(m,2H),7.16(ddd,J=8.2,5.2,3.1Hz,1H),4.21(s,2H),3.63(s,3H).
13C NMR(126MHz,Chloroform-d)δ190.90,150.95,148.84,141.34,132.30,130.49,127.26,126.18,125.29,125.25,121.22,121.19,120.40,118.84,118.79,108.76,108.74,84.07,83.99,34.10,34.08,27.87,27.85.
19F NMR(471MHz,Chloroform-d)δ-139.04.
1630
1H NMR(500MHz,Chloroform-d)δ7.60(s,1H),7.53(dt,J=7.9,1.1Hz,1H),7.28-7.26(m,1H),7.20(d,J=3.6Hz,2H),7.14(ddd,J=8.1,4.8,3.4Hz,1H),6.53(dd,J=3.6,1.7Hz,1H),4.17(s,2H),3.64(s,3H).
13C NMR(126MHz,Chloroform-d)δ185.72,152.22,150.24(d,J=266.3Hz),146.45,130.52,125.39,121.26,121.23,120.44,118.91,118.86,117.54,112.29,108.80,108.78,83.71,83.62,32.69,32.67,27.96,27.94.
19F NMR(471MHz,Chloroform-d)δ-139.01.
1488
1H NMR(500MHz,Chloroform-d)δ8.11-8.06(m,2H),7.59-7.53(m,1H),7.47(t,J=7.6Hz,2H),7.40(d,J=7.9Hz,1H),7.03-6.94(m,2H),4.30(s,2H),3.59(s,3H),2.48(s,3H).
13C NMR(126MHz,Chloroform-d)δ196.77,196.76,149.61(d,J=264.9Hz),136.40,133.07,131.05,131.02,130.90,128.61,128.54,123.09,123.04,121.94,118.64,118.59,108.97,83.81,83.72,33.01,32.99,27.88,27.86,21.87.
19F NMR(471MHz,Chloroform-d)δ-139.76.
1489
1H NMR(500MHz,Chloroform-d)δ8.09-8.05(m,2H),7.58-7.52(m,1H),7.46(dd,J=8.4,7.0Hz,2H),7.38(d,J=8.6Hz,1H),6.80(dd,J=8.7,2.3Hz,1H),6.70(d,J=2.3Hz,1H),4.28(s,2H),3.85(s,3H),3.57(s,3H).
13C NMR(126MHz,Chloroform-d)δ196.74,155.95,149.17(d,J=264.1Hz),136.36,133.08,131.28,128.61,128.52,119.73,119.68,119.36,109.27,93.69,83.70,83.62,55.88,32.96,32.94,27.98,27.97.
19F NMR(471MHz,Chloroform-d)δ-139.76.
1490
1H NMR(500MHz,Chloroform-d)δ8.11(d,J=8.0Hz,2H),7.77(s,1H),7.62(t,J=7.3Hz,1H),7.52(t,J=7.7Hz,2H),7.46(d,J=7.9Hz,1H),7.30(d,J=13.2Hz,2H),4.38(s,2H),3.71(s,3H).
13C NMR(126MHz,Chloroform-d)δ196.00,150.90(d,J=267.9Hz),136.26,133.34,132.07,128.73,128.44,125.04,123.00,118.13,118.10,118.07,116.48,116.46,109.11,109.10,85.29,85.20,32.44,32.42,28.24,28.22.
19F NMR(471MHz,Chldoroform-d)δ-60.38,-135.87.
1497
1H NMR(500MHz,Chloroform-d)δ8.10-8.03(m,2H),7.61-7.55(m,2H),7.48(dd,J=8.4,7.1Hz,2H),7.27(d,J=10.2Hz,1H),7.06(d,J=8.6Hz,1H),4.28(s,2H),3.61(s,3H).
13C NMR(126MHz,Chloroform-d)δ196.17,150.47(d,J=267.6Hz),136.25,133.29,129.28,128.70,128.46,127.09,124.15,124.12,121.46,121.41,113.66,110.46,110.44,84.13,84.04,32.56,32.54,28.14.
19F NMR(471MHz,Chloroform-d)δ-136.49.
1672
1H NMR(500MHz,Chloroform-d)δ8.07(dt,J=7.2,1.4Hz,2H),7.62-7.55(m,2H),7.49(dd,J=8.5,7.1Hz,2H),7.29-7.26(m,1H),7.07(d,J=8.6Hz,1H),4.28(s,2H),3.61(s,3H).
13C NMR(126MHz,Chloroform-d)δ196.13,150.47(d,J=267.5Hz),136.26,133.27,129.28,128.70,128.46,127.09,124.16,124.13,121.47,121.42,113.67,110.45,110.43,84.14,84.05,32.56,32.53,28.14,28.12.
19F NMR(471MHz,Chloroform-d)δ-136.51.
1561
1H NMR(500MHz,Chloroform-d)δ7.81(dt,J=7.8,0.9Hz,1H),7.49(s,2H),7.31-7.26(m,2H),7.22-7.18(m,1H),5.21(s,1H),3.71(s,3H),1.52(s,18H).
13C NMR(126MHz,Chloroform-d)δ152.13,148.77(d,J=268.1Hz),136.22,130.53,124.84,124.82,124.47,124.08,123.41,121.22,121.20,120.63,119.44,119.39,108.89,108.88,34.49,30.41,30.37,27.94,27.92.
1461
1H NMR(500MHz,Chloroform-d)δ7.67(s,1H),7.56(s,2H),7.22(d,J=8.2Hz,1H),7.14(dd,J=8.3,1.6Hz,1H),5.27(s,1H),3.72(s,3H),2.55(s,3H),1.60(s,19H).
13C NMR(126MHz,Chloroform-d)δ152.15,148.91(d,J=267.8Hz),136.24,129.93,128.86,124.97,124.95,124.71,123.67,123.64,122.65,122.63,119.38,119.33,108.72,108.71,34.57,30.49,28.00,27.98,21.87.
19F NMR(471MHz,Chloroform-d)δ-139.10.
1440
1H NMR(500MHz,Chloroform-d)δ7.92(d,J=1.9Hz,1H),7.45(s,2H),7.35(dd,J=8.6,1.9Hz,1H),7.15(d,J=8.5Hz,1H),5.27(s,1H),3.70(s,3H),1.54(s,18H).
13C NMR(126MHz,Chloroform-d)δ152.48,149.05(d,J=269.4Hz),136.43,129.16,124.89,124.87,124.13,124.10,122.68,122.65,122.11,122.06,113.92,110.48,34.51,30.41,28.11.
19F NMR(471MHz,Chloroform-d)δ-137.03.
1458
1H NMR(500MHz,Chloroform-d)δ7.33(s,2H),7.20(dd,J=6.0,3.2Hz,1H),7.16-7.13(m,2H),5.23(s,1H),3.72(s,3H),1.50(s,18H).
13C NMR(126MHz,Chloroform-d)δ152.81,149.44(d,J=266.9Hz),134.77,131.57,128.31,126.19,122.04,121.85,121.54,121.39,121.36,107.52,95.21,34.38,30.48,28.20.
19F NMR(471MHz,Chloroform-d)δ-137.89.
1615
1H NMR(500MHz,Chloroform-d)δ7.47(d,J=8.0Hz,1H),7.24-7.19(m,2H),7.16-7.11(m,1H),3.96(q,J=7.1Hz,1H),3.66(s,3H),2.52-2.35(m,2H),1.50(d,J=7.0Hz,3H),0.98(t,J=7.3Hz,3H).
13C NMR(126MHz,Chloroform-d)δ211.32,148.56,130.54,124.29,124.25,121.27,121.24,120.45,119.07,119.02,108.90,108.88,90.26,90.18,41.51,41.49,33.49,27.91,27.90,15.39,8.05.
19F NMR(471MHz,Chloroform-d)δ-138.87.
1620
1H NMR(500MHz,Chloroform-d)δ7.42(dd,J=7.8,1.0Hz,1H),7.24-7.20(m,2H),7.16(ddd,J=8.1,5.5,2.8Hz,1H),3.72(s,2H),3.66(s,3H),2.18(s,3H).
13C NMR(126MHz,Chloroform-d)δ206.32,150.21(d,J=266.2Hz),130.56,125.26,121.38,121.36,120.51,118.48,118.43,108.92,108.91,84.08,83.99,37.71,37.69,28.73,27.97.27.96.
19F NMR(471MHz,Chloroform-d)δ-139.61.
1651
1H NMR(500MHz,Chloroform-d)δ7.41(d,J=7.8Hz,1H),7.23-7.18(m,2H),7.14(ddd,J=8.1,5.5,2.7Hz,1H),3.86(s,2H),3.63(s,3H),1.28(s,9H).
13C NMR(126MHz,Chloroform-d)δ212.28,150.23(d,J=265.4Hz),130.56,125.61,125.56,121.06,121.03,120.23,118.71,118.66,108.80,108.78,84.51,84.43,44.46,30.47,30.44,27.91,27.89,26.62.
19F NMR(471MHz,Chloroform-d)δ-139.58.
1678
1H NMR(500MHz,Chloroform-d)δ7.42(d,J=7.8Hz,1H),7.24-7.19(m,2H),7.15(ddd,J=8.1,5.4,2.8Hz,1H),3.70(s,2H),3.65(s,3H),2.47(t,J=7.4Hz,2H),1.57(p,J=7.3Hz,2H),1.23(s,8H),0.87(t,J=6.9Hz,3H).
13C NMR(126MHz,Chloroform-d)δ208.51,150.22(d,J=266.0Hz),130.55,125.32,121.31,121.28,120.45,118.57,118.52,108.85,108.84,84.20,84.12,41.34,36.88,36.85,31.66,29.11,29.04,27.96,27.94,23.86,22.59,14.06.
19F NMR(471MHz,Chloroform-d)δ-139.70.
1737
1H NMR(500MHz,Chloroform-d)δ7.44-7.40(m,1H),7.25-7.20(m,2H),7.16(ddd,J=8.1,5.7,2.6Hz,1H),3.78(s,2H),3.67(s,3H),2.55(tt,J=11.5,3.5Hz,1H),1.93-1.87(m,2H),1.83-1.78(m,2H),1.47-1.39(m,2H),1.34-1.20(m,4H).
13C NMR(126MHz,Chloroform-d)δ210.92,150.24(d,J=265.9Hz),130.55,125.45,121.20,121.17,120.36,118.62,118.57,108.81,108.80,84.13,84.04,49.49,34.72,34.70,28.67,27.96,25.86,25.67.
19F NMR(471MHz,Chloroform-d)δ-139.67.
1511
1H NMR(500MHz,Chloroform-d)δ7.89(d,J=7.7Hz,1H),7.68(td,J=7.5,1.3Hz,1H),7.55(d,J=7.7Hz,1H),7.46(t,J=7.5Hz,1H),7.22(d,J=8.2Hz,1H),7.17(ddd,J=8.2,5.9,2.3Hz,1H),7.04-6.97(m,2H),4.16(dd,J=8.6,4.9Hz,1H),3.71-3.66(m,1H),3.64(s,3H),3.38(dd,J=17.3,4.8Hz,1H).
13C NMR(126MHz,Chloroform-d)δ206.12,153.47,150.36(d,J=266.2Hz),136.41,135.10,130.67,127.69,126.58,124.37,124.09,121.25,121.22,120.29,118.58,118.53,109.04,88.77,88.69,42.77,42.74,34.21,27.92,27.91.
19F NMR(471MHz,Chloroform-d)δ-139.05.
1793
1H NMR(500MHz,Chloroform-d)δ8.16(dd,J=7.8,1.4Hz,1H),7.54(td,J=7.5,1.5Hz,1H),7.40-7.35(m,1H),7.33(ddd,J=7.8,2.4,1.4Hz,2H),7.25-7.18(m,2H),7.10(ddd,J=8.1,6.9,1.3Hz,1H),4.08(dd,J=12.6,4.6Hz,1H),3.65(s,3H),3.22(ddd,J=16.4,11.8,4.4Hz,1H),3.10(dt,J=16.6,4.0Hz,1H),2.69-2.59(m,1H),2.41(dq,J=13.2,4.3Hz,1H).
13C NMR(126MHz,Chloroform-d)δ197.15,149.84(d,J=265.9Hz),144.22,133.42,132.79,130.66,128.78,127.98,126.77,124.70,121.02,120.99,120.16,119.05,119.00,108.97,108.96,44.45,44.43,30.54,29.64,27.90,27.88.
19F NMR(471MHz,Chloroform-d)δ-137.74.
1679
1H NMR(500MHz,Chloroform-d)δ7.64(dd,J=7.8,1.1Hz,1H),7.21-7.17(m,2H),7.14(ddd,J=8.1,5.6,2.8Hz,1H),3.90(dd,J=12.2,3.0Hz,1H),3.62(s,3H),2.76(ddd,J=12.5,8.3,5.9Hz,1H),2.70-2.60(m,1H),2.35-2.25(m,1H),2.14-2.06(m,1H),1.96-1.89(m,2H),1.81-1.73(m,2H),1.64(dtt,J=9.7,3.8,2.1Hz,2H),1.56-1.49(m,1H),1.43(dddd,J=11.4,9.8,3.8,2.4Hz,1H),0.93-0.77(m,1H).
13C NMR(126MHz,Chloroform-d)δ215.23,149.95(d,J=267.3Hz),130.33,121.24,121.21,120.38,119.40,119.35,108.67,108.66,48.70,48.67,39.38,29.13,29.12,27.87,27.85,27.77,27.13,26.40,24.70.
19F NMR(471MHz,Chloroform-d)δ-135.56.
1621
1H NMR(500MHz,Chloroform-d)δ7.61-7.55(m,1H),7.23-7.18(m,2H),7.16(td,J=5.5,2.9Hz,1H),4.89(t,J=2.0Hz,2H),4.51(t,J=2.0Hz,2H),4.15(s,5H),4.05(s,2H),3.66(s,3H).
13C NMR(126MHz,Chloroform-d)δ200.93,149.64(d,J=333.6Hz),130.51,121.25,121.23,120.45,119.14,119.09,108.79,84.93,72.31,69.85,69.63,34.00,33.97,28.00.
19F NMR(471MHz,Chloroform-d)δ-139.24.
1756
1H NMR(500MHz,Chloroform-d)δ7.40(d,J=7.8Hz,1H),7.23-7.19(m,2H),7.14(ddd,J=8.1,4.9,3.4Hz,1H),3.63(s,3H),3.57(d,J=4.4Hz,1H),2.85(d,J=4.8Hz,2H),1.98-1.88(m,2H),1.83-1.77(m,1H),1.74(dd,J=10.4,1.6Hz,1H),1.62-1.56(m,2H).
13C NMR(126MHz,Chloroform-d)δ216.42,151.10,148.98,130.51,125.73,121.23,121.20,120.26,118.21,118.16,108.86,108.85,86.13,50.96,50.16,50.13,41.70,37.03,27.93,27.91,25.41,22.47.
19F NMR(471MHz,Chloroform-d)δ-135.13.
1628
1H NMR(500MHz,Chloroform-d)δ7.39(d,J=7.7Hz,1H),7.21(dd,J=3.9,1.4Hz,2H),7.14(ddd,J=8.1,5.3,3.1Hz,1H),3.82(s,2H),3.63(s,3H),2.12(s,3H),1.98(s,6H),1.83-1.73(m,6H).
13C NMR(126MHz,Chloroform-d)δ196.28,150.02(d,J=265.9Hz),145.76,139.91,135.06,130.62,129.13,128.97,128.24,127.28,127.27,121.27,121.24,120.46,118.90,118.85,108.84,84.16,32.99,32.96,27.98.
19F NMR(471MHz,Chloroform-d)δ-139.58.
1772
1H NMR(500MHz,Chloroform-d)δ7.39(d,J=7.8Hz,1H),7.22-7.17(m,2H),7.12(ddd,J=8.1,5.8,2.4Hz,1H),5.34(dd,J=4.9,2.5Hz,1H),3.76-3.69(m,2H),3.64(s,3H),3.56-3.48(m,1H),2.71(t,J=9.0Hz,1H),2.40-2.06(m,5H),2.00(ddt,J=14.9,5.2,2.7Hz,1H),1.89-1.82(m,2H),1.71-1.59(m,5H),1.51(tdd,J=14.1,8.7,4.0Hz,5H),1.27-1.21(m,2H),1.17-1.07(m,2H),1.02(s,4H),0.71(s,3H).
13C NMR(126MHz,Chloroform-d)δ208.19,150.19(d,J=266.0Hz),140.81,130.54,121.40,121.17,121.14,120.35,118.71,118.66,108.81,108.79,71.71,61.31,56.95,50.03,44.43,42.26,38.91,38.24,38.22,37.31,36.56,31.92,31.82,31.63,27.96,24.63,23.52,21.21,19.42.13.54.
19F NMR(471MHz,Chloroform-d)δ-139.31.
1792
1H NMR(500MHz,Chloroform-d)δ7.38(d,J=7.8Hz,1H),7.20(dd,J=5.3,1.7Hz,2H),7.15-7.12(m,1H),5.74(d,J=1.7Hz,1H),3.70(d,J=7.6Hz,1H),3.64(s,3H),2.71(t,J=9.0Hz,1H),2.46-2.35(m,3H),2.35-2.24(m,4H),2.22-2.12(m,2H),2.04(ddd,J=13.4,5.1,3.2Hz,1H),1.85(ddt,J=12.9,5.6,2.8Hz,1H),1.69-1.65(m,2H),1.51-1.45(m,2H),1.23-1.12(m,6H),1.08-1.02(m,1H),0.99(dd,J=11.8,3.9Hz,1H),0.90(dd,J=14.9,7.7Hz,1H),0.74(s,3H).
13C NMR(126MHz,Chloroform-d)δ208.02,199.52,171.05,150.18(d,J=265.7Hz),130.54,129.59,125.79,125.45,123.93,121.22,121.19,120.38,118.66,118.61,108.85,84.09,84.01,61.07,56.05,53.66,44.35,38.69,38.61,38.23,38.20,35.75,35.59,33.97,32.81,31.95,27.97,27.96,24.50,23.88,23.53,21.13,19.74,17.39,13.64.
19F NMR(471MHz,Chloroform-d)δ-139.33.
1838
1H NMR(500MHz,Chloroform-d)δ7.34(dt,J=7.8,1.0Hz,2H),7.25-7.20(m,4H),7.14(ddd,J=8.2,6.3,1.9Hz,2H),3.80(s,4H),3.60(s,7H).
13C NMR(126MHz,Chloroform-d)δ205.50,150.24(d,J=266.3Hz),130.56,125.32,125.27,121.28,121.25,120.39,118.50,118.45,108.81,83.95,83.86,35.66,35.64,27.87,27.86.
19F NMR(471MHz,Chloroform-d)δ-139.43.
1860
1H NMR(500MHz,Chloroform-d)δ7.52(d,J=7.8Hz,1H),7.23-7.20(m,2H),7.19-7.14(m,1H),4.18(q,J=7.1Hz,2H),3.69(s,2H),3.64(s,3H),1.27(t,J=7.1Hz,3H).
13C NMR(126MHz,Chloroform-d)δ171.33,171.31,151.25,149.13,130.46,125.33,125.29,121.20,121.18,120.33,118.71,118.66,108.80,108.79,83.93,83.85,60.91,28.35,28.33,27.91,27.89,14.24.
19F NMR(471MHz,Chloroform-d)δ-139.50.
1893
1H NMR(500MHz,Chloroform-d)δ7.54-7.49(m,1H),7.22-7.18(m,2H),7.14(ddd,J=8.1,5.4,2.8Hz,1H),3.64(s,3H),3.59(s,2H),1.45(s,9H).
13C NMR(126MHz,Chloroform-d)δ170.62,150.15(d,J=266.3Hz),130.47,125.44,125.40,121.07,121.04,120.19,118.80,118.75,108.72,108.71,84.43,84.34,80.85,29.72,29.56,29.54,28.07,27.90,27.88.
19F NMR(471MHz,Chloroform-d)δ-139.69.
Jing
1H NMR(500MHz,Chloroform-d)δ7.57(dt,J=7.7,1.0Hz,1H),7.30-7.19(m,3H),3.75(d,J=0.8Hz,2H),3.64(s,3H).
13C NMR(126MHz,Chloroform-d)δ149.70(d,J=267.8Hz),130.36,123.97,123.93,121.97,121.95,121.00,118.04,117.99,117.27,109.20,109.18,79.77,79.69,28.02,28.00,11.27,11.25.
19F NMR(471MHz,Chloroform-d)δ-138.09.
1622
1H NMR(500MHz,Chloroform-d)δ8.12-8.02(m,2H),7.58-7.53(m,1H),7.52-7.49(m,1H),7.47(dd,J=8.4,7.0Hz,2H),7.24-7.17(m,2H),7.14(ddd,J=8.1,6.6,1.7Hz,1H),4.32(s,2H),4.09(t,J=6.7Hz,2H),3.36(t,J=6.5Hz,2H),2.01-1.90(m,2H),1.86-1.75(m,2H).
13C NMR(126MHz,Chloroform-d)δ196.60,149.77(d,J=265.8Hz),136.36,133.12,129.78,128.63,128.48,125.58,125.53,121.37,121.34,120.49,119.07,119.02,108.97,84.41,84.32,41.24,32.95,32.93,32.80,29.74,28.22.
19F NMR(471MHz,Chloroform-d)δ-138.37.
1755
1H NMR(500MHz,Chloroform-d)δ8.65(d,J=1.7Hz,1H),8.12(dd,J=8.6,1.8Hz,1H),8.00(dd,J=8.2,1.3Hz,1H),7.90(t,J=8.7Hz,2H),7.65-7.56(m,3H),7.24-7.16(m,3H),4.47(s,2H),4.11(t,J=6.8Hz,2H),3.33(t,J=6.5Hz,2H),2.00-1.92(m,2H),1.85-1.78(m,2H).
13C NMR(126MHz,Chloroform-d)δ196.61,149.76(d,J=265.3Hz),135.60,133.64,132.53,130.19,129.79,129.63,128.50,128.45,127.79,126.77,124.26,121.40,121.37,120.53,119.12,119.07,108.99,41.25,33.12,33.10,32.78,29.72,28.21.
19F NMR(471MHz,Chloroform-d)δ-138.24.
1637
1H NMR(500MHz,Chloroform-d)δ8.04(d,J=8.7Hz,2H),7.51(d,J=7.8Hz,1H),7.22-7.15(m,2H),7.15-7.10(m,1H),6.93(d,J=8.8Hz,2H),4.25(s,2H),4.09(t,J=6.8Hz,2H),3.86(s,3H),3.37(t,J=6.5Hz,2H),1.95(p,J=6.7Hz,2H),1.84(dq,J=13.1,6.4Hz,2H).
13C NMR(126MHz,Chloroform-d)δ195.23,163.49,150.73,130.77,129.76,129.40,125.61,121.30,121.28,120.44,119.16,119.11,113.76,108.90,84.71,55.47,41.23,32.78,32.69,32.67,29.77,28.24.
19F NMR(471MHz,Chloroform-d)δ-138.60.
1634
1H NMR(500MHz,Chloroform-d)δ7.78(dd,J=7.7,1.4Hz,1H),7.47(d,J=7.6Hz,1H),7.35(td,J=7.5,1.4Hz,1H),7.26(s,1H),7.23-7.17(m,3H),7.16-7.11(m,1H),4.24(s,2H),4.07(t,J=6.8Hz,2H),3.35(t,J=6.5Hz,2H),2.45(s,3H).
13C NMR(126MHz,Chloroform-d)δ200.81,149.91(d,J=265.8Hz),138.59,137.37,131.96,131.24,129.73,128.44,125.55,121.33,121.30,120.45,118.88,118.83,108.99,84.53,84.44,41.20,35.69,35.67,32.80,29.66,28.17,21.22.
19F NMR(471MHz,Chloroform-d)δ-138.61.
1635
1H NMR(500MHz,Chloroform-d)δ7.73(dd,J=6.7,2.4Hz,1H),7.59-7.53(m,2H),7.47(d,J=7.9Hz,1H),7.44-7.40(m,1H),7.27-7.21(m,2H),7.18(ddd,J=8.1,6.4,1.9Hz,1H),4.21(s,2H),4.10(t,J=6.8Hz,2H),3.39(t,J=6.5Hz,2H),2.01-1.91(m,2H),1.86-1.75(m,2H).
13C NMR(126MHz,Chloroform-d)δ200.80,150.22(d,J=266.9Hz),139.67,131.63,129.99,129.70,127.22,126.70,126.66,125.38,121.46,121.43,120.60,118.71,118.66,109.02,83.20,83.11,41.22,37.08,32.73,29.66,28.17.
19F NMR(471MHz,Chloroform-d)δ-57.95,-138.35.
1636
1H NMR(500MHz,Chloroform-d)δ8.63(d,J=1.8Hz,1H),8.10(dd,J=8.5,1.8Hz,1H),7.97(d,J=8.0Hz,1H),7.88(t,J=8.7Hz,2H),7.58(dddd,J=14.9,9.4,6.8,1.3Hz,3H),7.23-7.13(m,3H),4.45(s,2H),4.08(t,J=6.8Hz,2H),3.30(t,J=6.5Hz,2H),1.93(p,J=6.8Hz,2H),1.86-1.74(m,2H).
13C NMR(126MHz,Chloroform-d)δ196.63,149.77(d,J=265.5Hz),135.60,133.64,132.54,130.20,129.79,129.64,128.51,128.46,127.79,126.78,124.26,121.41,121.38,120.54,119.13,119.07,109.01,41.25,33.12,33.10,32.81,29.72,28.21.
19F NMR(471MHz,Chloroform-d)δ-138.22.
1654
1H NMR(500MHz,Chloroform-d)δ7.81(d,J=8.5Hz,2H),7.75(d,J=8.5Hz,2H),7.48(dd,J=7.8,1.2Hz,1H),7.23-7.17(m,2H),7.14(ddd,J=8.1,6.4,1.9Hz,1H).
13C NMR(126MHz,Chlotoform-d)δ195.94,149.68(d,J=265.7Hz),137.93,135.52,129.88,129.76,121.49,121.46,120.59,118.96,118.91,109.04,101.08,84.07,83.98,41.28,32.96,32.94,32.73,29.75,28.22.
19F NMR(471MHz,Chloroform-d)δ-138.22.
1655
1H NMR(500MHz,Chloroform-d)δ8.10(dd,J=8.3,1.3Hz,2H),7.61-7.56(m,1H),7.49(t,J=7.7Hz,2H),7.35-7.32(m,1H),7.13(d,J=8.2Hz,1H),7.04(dd,J=8.3,1.6Hz,1H),4.32(s,2H),4.08(t,J=6.7Hz,2H),3.38(t,J=6.5Hz,2H),2.46(s,3H),2.00-1.92(m,2H),1.87-1.80(m,2H).
13C NMR(126MHz,Chloroform-d)δ196.71,149.81(d,J=265.5Hz),136.37,133.09,129.86,128.61,128.51,128.01,122.78,122.75,118.90,118.85,108.76,41.24,33.02,32.99,32.84,29.73,28.21,21.58.
19F NMR(471MHz,Chloroform-d)δ-138.22.
1656
1H NMR(500MHz,Chloroform-d)δ8.05(d,J=7.0Hz,2H),7.56-7.51(m,1H),7.45(dd,J=8.4,7.0Hz,2H),7.38(d,J=8.0Hz,1H),7.00(s,1H),6.96(dd,J=8.1,1.4Hz,1H),4.28(s,2H),4.05(t,J=6.7Hz,2H),3.36(t,J=6.5Hz,2H),2.45(s,3H),1.98-1.90(m,2H),1.87-1.77(m,2H).
13C NMR(126MHz,Chloroform-d)δ196.70,149.34(d,J=264.9Hz),136.35,133.04,131.16,131.13,130.03,128.58,128.48,122.00,118.82,118.77,109.04,41.13,33.07,33.05,32.82,29.75,28.20,21.88.
19F NMR(471MHz,Chloroform-d)δ-139.28.
1693
1H NMR(500MHz,Chloroform-d)δ8.14(d,J=8.3Hz,2H),7.69(d,J=8.4Hz,2H),7.65-7.60(m,2H),7.54(dd,J=7.6,1.2Hz,1H),7.48(t,J=7.5Hz,2H),7.43-7.38(m,1H),7.25-7.18(m,2H),7.16(ddd,J=8.2,6.6,1.8Hz,1H),4.35(s,2H),4.10(t,J=6.8Hz,2H),3.37(t,J=6.5Hz,2H),2.01-1.92(m,2H),1.90-1.78(m,2H).
13C NMR(126MHz,Chloroform-d)δ196.19,149.77(d,J=265.7Hz),145.77,139.88,135.03,129.10,128.98,128.26,127.28,127.26,121.39,121.37,120.52,119.11,119.06,108.98,41.27,33.04,33.02,32.80,29.77,28.25.
19F NMR(471MHz,Chloroform-d)δ-138.34.
1680
1H NMR(500MHz,Chloroform-d)δ8.11-8.04(m,2H),7.60-7.53(m,1H),7.52-7.45(m,3H),7.31-7.28(m,1H),7.23-7.18(m,1H),7.14(td,J=7.6,1.1Hz,1H),4.32(s,2H),4.24(t,J=6.6Hz,2H),3.33(t,J=6.3Hz,2H),2.37-2.29(m,2H).
13C NMR(126MHz,Chloroform-d)δ196.51,149.78(d,J=266.3Hz),136.34,133.15,129.97,128.64,128.47,125.60,125.55,121.52,121.50,120.63,119.09,119.04,109.02,84.71,84.62,40.24,32.88,32.85,32.61,29.90.
19F NMR(471MHz,Chloroform-d)δ-138.18.
1716
1H NMR(500MHz,Chloroform-d)δ7.41(d,J=7.8Hz,1H),7.25(t,J=7.2Hz,4H),7.23-7.19(m,1H),7.19-7.16(m,1H),7.16-7.13(m,2H),4.12(t,J=6.8Hz,2H),3.72(s,2H),3.40(t,J=6.4Hz,2H),2.95-2.88(m,2H),2.87-2.79(m,2H),2.05-1.95(m,2H),1.94-1.83(m,2H).
13C NMR(126MHz,Chloroform-d)δ207.16,149.99(d,J=266.0Hz),141.01,129.74,128.44,128.32,126.07,121.49,121.47,120.57,118.71,118.66,109.03,42.84,41.28,37.11,37.09,32.72,29.84,29.78,28.25.
19F NMR(471MHz,Chloroform-d)δ-139.10.
the above description is only a preferred embodiment of the present invention, and therefore should not be taken as limiting the scope of the invention, which is defined by the appended claims.
Claims (10)
1. A synthetic method of 2-fluoroindole compounds is characterized by comprising the following steps: the method comprises the following steps:
(1) adding an o-aminochalcone compound, bromodifluoroacetic acid ethyl ester, alkali and an organic solvent into a pressure-resistant sealed reaction vessel, and stirring and reacting for 10-15h at 50-100 ℃ in a nitrogen atmosphere; the structural formula of the o-amino chalcone compound is one of the following formulas:
(2) cooling the material obtained in the step (1) to room temperature, adding ethyl acetate, fully mixing, and sequentially filtering and washing with ethyl acetate to obtain an organic phase;
(3) and (3) carrying out spin drying on the organic solvent in the organic phase obtained in the step (2), and then carrying out purification and elution by an eluent to obtain the 2-fluoroindole compound.
2. The method of synthesis of claim 1, wherein: the alkali is potassium phosphate, potassium carbonate, potassium hydroxide, cesium carbonate, sodium carbonate or sodium hydroxide.
3. The method of synthesis of claim 2, wherein: the base is potassium phosphate.
4. The method of synthesis of claim 1, wherein: the organic solvent is acetonitrile, 1, 4-dioxane, acetone or tetrahydrofuran.
5. The method of synthesis of claim 4, wherein: the organic solvent is acetonitrile.
6. The method of synthesis of claim 1, wherein: the eluent consists of petroleum ether and dichloromethane.
7. The method of synthesis of claim 6, wherein: the volume ratio of the petroleum ether to the dichloromethane is 1-5: 1.
8. The method of synthesis of claim 7, wherein: the volume ratio of the petroleum ether to the dichloromethane is 5: 1.
9. The method of synthesis of claim 1, wherein: the proportion of the o-amino chalcone compound, the bromodifluoroacetic acid ethyl ester, the alkali and the organic solvent is 0.1-0.3 mmol: 0.5-1 mmol: 1.5-2.5 mL.
10. The method of synthesis of claim 9, wherein: the proportion of the o-amino chalcone compound, the bromodifluoroacetic acid ethyl ester, the alkali and the organic solvent is 0.2 mmol: 0.6 mmol: 2 mL.
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