CN110028438B - Synthetic method of 3-phenyl-3-indole trifluoromethyl propyl ketone derivative - Google Patents
Synthetic method of 3-phenyl-3-indole trifluoromethyl propyl ketone derivative Download PDFInfo
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000012043 crude product Substances 0.000 claims abstract description 14
- YKDOAIQSCBPJKV-UHFFFAOYSA-N 4,4,4-trifluoro-3-phenylbutan-2-one Chemical compound CC(=O)C(C(F)(F)F)C1=CC=CC=C1 YKDOAIQSCBPJKV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims abstract description 12
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims abstract description 12
- 150000002475 indoles Chemical class 0.000 claims abstract description 10
- 239000003208 petroleum Substances 0.000 claims abstract description 9
- 239000000047 product Substances 0.000 claims abstract description 9
- 229940045803 cuprous chloride Drugs 0.000 claims abstract description 8
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 7
- 239000012074 organic phase Substances 0.000 claims abstract description 7
- 238000000926 separation method Methods 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000003760 magnetic stirring Methods 0.000 claims abstract description 3
- 238000000746 purification Methods 0.000 claims abstract description 3
- 239000003480 eluent Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 16
- 229940079593 drug Drugs 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 10
- 239000000575 pesticide Substances 0.000 abstract description 5
- 239000000543 intermediate Substances 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 230000004071 biological effect Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 238000005839 oxidative dehydrogenation reaction Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- BLRHMMGNCXNXJL-UHFFFAOYSA-N 1-methylindole Chemical compound C1=CC=C2N(C)C=CC2=C1 BLRHMMGNCXNXJL-UHFFFAOYSA-N 0.000 description 1
- YDLOPHRVGMIZDX-UHFFFAOYSA-N 6-chloro-1-methylindole Chemical compound C1=C(Cl)C=C2N(C)C=CC2=C1 YDLOPHRVGMIZDX-UHFFFAOYSA-N 0.000 description 1
- CPNRIIXMZIMPLB-UHFFFAOYSA-N 6-fluoro-1-methylindole Chemical compound C1=C(F)C=C2N(C)C=CC2=C1 CPNRIIXMZIMPLB-UHFFFAOYSA-N 0.000 description 1
- VTJXLVGZNOINAD-UHFFFAOYSA-N 6-methoxy-1-methylindole Chemical compound COC1=CC=C2C=CN(C)C2=C1 VTJXLVGZNOINAD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000037081 physical activity Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a synthetic method of a 3-phenyl-3-indole trifluoromethyl acetone compound, belonging to the technical field of organic synthesis intermediates, and the method specifically comprises the following steps: 1) adding indole derivatives, 3-phenyl trifluoromethyl acetone, cuprous chloride and 1, 2-dichloroethane into a reaction tube, and reacting for 4 hours at 80 ℃ under magnetic stirring in air atmosphere; 2) after the reaction is finished, extracting with ethyl acetate, combining organic phases, distilling under reduced pressure to remove most of the solvent to obtain a crude product, and performing column chromatography separation and purification on the crude product by taking petroleum ether and ethyl acetate with the volume ratio of 10:1 as leacheate to obtain a target product. The method has wide application in the fields of medicines, pesticides, chemical industry, organic synthesis and the like, and has the advantages of simple operation, mild reaction conditions, low cost, high yield and better application prospect.
Description
Technical Field
The invention belongs to the field of organic synthesis intermediates, and particularly relates to a method for synthesizing a 3-phenyl-3-indole trifluoromethyl acetone derivative by using oxidative dehydrogenation coupling reaction catalyzed by transition metal.
Background
The organic fluoride has unique physical and biological activity, and is widely applied to the fields of medicines, materials and the like. Many drug molecules contain trifluoromethyl functional groups that can enhance the biological activity of the molecule, such as lipid solubility, lipophilicity, selectivity, and the like. In recent years, introduction of a trifluoromethyl functional group into an organic molecule has been one of the research fields of hot spots. In addition, indole compounds are a very important heterocyclic compound containing nitrogen atoms, and widely exist in natural products and drug molecules. Generally, from the perspective of designing pharmaceutically active molecules, two biologically active fragments are constructed in a single small molecule, which can greatly improve the biological activity of the molecule.
Because of the wide application of the 3-phenyl-3-indole trifluoromethyl acetone derivative in the field of fine organic synthesis and the wide application prospect of the derivative in medicines and pesticides, the synthesis method of the compound is noted. Therefore, the method for exploring a green transition metal catalytic oxidative dehydrogenation coupling reaction is applied to the synthesis of the 3-phenyl-3-indole trifluoromethyl acetone derivative, and has important significance.
Disclosure of Invention
The invention aims to search a green synthetic method which is easy to operate, efficiently synthesize the 3-phenyl-3-indole trifluoromethyl acetone derivative under a mild condition and obtain a better yield.
In order to realize the purpose of the invention, the following scheme is adopted for realizing the purpose: a method for synthesizing a 3-phenyl-3-indole trifluoromethyl acetone derivative compound,
the reaction equation is:
R1is methoxy, chlorine, fluorine; r2Is methyl, hydrogen.
The method specifically comprises the following steps:
1) adding indole derivatives, 3-phenyl trifluoromethyl acetone, cuprous chloride and 1, 2-dichloroethane into a reaction tube, and magnetically stirring at 80 ℃ for reaction for 4 hours in air atmosphere;
2) and after the reaction is finished, extracting by ethyl acetate, combining organic phases, removing most of solvent by reduced pressure distillation to obtain a crude product, and performing column chromatography separation and purification on the crude product by taking a mixed solution of petroleum ether and ethyl acetate as an eluent to obtain a target product.
Preferably, the method comprises the following steps: the mol ratio of the indole derivative to the 3-phenyl trifluoromethyl acetone is as follows: 3: 2.
preferably, the method comprises the following steps: the volume ratio of the petroleum ether to the ethyl acetate is 10: 1.
Compared with the existing synthesis method, the invention has the beneficial effects that:
1) according to the invention, indole derivatives and 3-phenyl trifluoromethyl acetone are used as raw materials, a series of 3-phenyl-3-indole trifluoromethyl acetone derivatives are efficiently synthesized under the catalysis of cuprous chloride, and the yield is considerable;
2) the compound contains an indole skeleton and a trifluoromethyl functional group, can be used as an organic synthesis intermediate, has the advantages of good group tolerance, wide substrate expansion range and the like, can be widely used in the fields of pesticides, medicines and the like, and provides an effective fragment for the synthesis of novel medicines;
3) the invention adopts catalytic amount of cuprous chloride to promote the synthesis of the 3-phenyl-3-indole trifluoromethyl acetone derivative, thereby greatly improving the product yield and shortening the reaction time.
Drawings
FIG. 1 is a drawing showing the preparation of 3-phenyl-3- (N-methylindole) trifluoromethylacetone prepared in example 11Nuclear magnetic resonance spectrum by H-NMR;
FIG. 2 is a drawing showing the preparation of 3-phenyl-3- (N-methyl-6' -chloroindole) trifluoromethylacetone prepared in example 21Nuclear magnetic resonance spectrum of H-NMR;
FIG. 3 is a schematic representation of 3-phenyl-3- (N-methyl-6' -fluoroindole) trifluoromethylacetone prepared in example 31Nuclear magnetic resonance spectrum by H-NMR;
FIG. 4 shows the preparation of 3-phenyl-3- (N-methyl-6' -methoxyindole) trifluoromethylacetone prepared in example 41Nuclear magnetic resonance spectrum of H-NMR.
Detailed Description
The invention takes indole derivatives and 3-phenyl trifluoromethyl acetone as raw materials, and the mol ratio of the indole derivatives to the 3-phenyl trifluoromethyl acetone is as follows: 3: 2, catalyzing and realizing two different carbon-hydrogen bonds (sp) by using cuprous chloride2C-H and sp3C-H) can efficiently synthesize the 3-phenyl-3-indole trifluoromethyl acetone derivative.
Example 1: synthesis of 3-phenyl-3- (N-methylindole) trifluoromethylacetone
N-methylindole (0.3mmol, 39.3mg), 3-phenyltrifluoromethylacetone (0.2mmol, 37.6mg), CuCl (0.2eq, 4.0mg), and 1, 2-dichloroethane (2mL) were added to a 25mL reaction tube, and the reaction was magnetically stirred at 80 ℃ for 4 hours under an air atmosphere; after the reaction is finished, extracting by using ethyl acetate, combining organic phases, decompressing and steaming most of solvent to obtain a crude product, and performing reaction by using petroleum ether: and (3) performing column chromatography separation on the crude product by taking ethyl acetate (10:1) as eluent, and purifying to obtain a target product which is a reddish brown solid with the yield of 85%.
The nuclear magnetic data are as follows:
1H NMR(300MHz,CDCl3)δ＝7.80(d,J＝7.8Hz,2H),7.48-7.32(m,4H),7.27-7.20(m,3H),7.06-7.01(t,J＝7.8Hz,1H),5.38(s,1H),3.84(s,3H)。
example 2: synthesis of 3-phenyl-3- (N-methyl-6' -chloroindole) trifluoromethylacetone
N-methyl-6-chloroindole (0.3mmol, 49.5mg), 3-phenyltrifluoromethylacetone (0.2mmol, 37.6mg), CuCl (0.2eq, 4.0mg), and 1, 2-dichloroethane (2mL) were added to a 25mL reaction tube, and the reaction was magnetically stirred at 80 ℃ for 4 hours under an air atmosphere; after the reaction is finished, extracting by using ethyl acetate, combining organic phases, decompressing and steaming most of solvent to obtain a crude product, and performing reaction by using petroleum ether: and (3) performing column chromatography separation on the crude product by using ethyl acetate (10:1) as eluent, and purifying to obtain a target product which is a reddish brown solid with the yield of 68%.
The nuclear magnetic data are as follows:
1H NMR(300MHz,CDCl3)δ＝7.83(d,J＝7.8Hz,2H),7.50-7.45(t,J＝7.5Hz,1H),7.37(d,J＝5.4Hz,2H),7.33-7.22(m,3H),7.16(d,J＝8.7Hz,1H),5.28(s,1H),3.83(s,3H)。
example 3: synthesis of 3-phenyl-3- (N-methyl-6' -fluoroindole) trifluoromethylacetone
N-methyl-6-fluoroindole (0.3mmol, 44.7mg), 3-phenyltrifluoromethylacetone (0.2mmol, 37.6mg), CuCl (0.2eq, 4.0mg), and 1, 2-dichloroethane (2mL) were added to a 25mL reaction tube and reacted under magnetic stirring at 80 ℃ for 4 hours under an air atmosphere; after the reaction is finished, extracting by ethyl acetate, combining organic phases, decompressing and steaming to remove most of solvent to obtain a crude product, and extracting by petroleum ether: and (3) performing column chromatography separation on the crude product by using ethyl acetate (10:1) as eluent, and purifying to obtain a target product which is a reddish brown solid with the yield of 65%.
The nuclear magnetic data are as follows:
1H NMR(300MHz,CDCl3)δ＝7.78(d,J＝7.8Hz,2H),7.50-7.41(m,2H),7.28-7.21(m,3H),7.05-6.92(m,2H),5.28(s,1H),3.84(s,3H)。
example 4: synthesis of 3-phenyl-3- (N-methyl-6' -methoxyindole) trifluoromethylacetone
N-methyl-6-methoxyindole (0.3mmol, 48.3mg), 3-phenyltrifluoromethylacetone (0.2mmol, 37.6mg), CuCl (0.2eq, 4.0mg), and 1, 2-dichloroethane (2mL) were added to a 25mL reaction tube, and the reaction was magnetically stirred at 80 ℃ for 4 hours under an air atmosphere; after the reaction is finished, extracting by using ethyl acetate, combining organic phases, decompressing and steaming most of solvent to obtain a crude product, and performing reaction by using petroleum ether: and (3) performing column chromatography separation on the crude product by using ethyl acetate (10:1) as eluent, and purifying to obtain a target product which is a reddish brown solid with the yield of 78%.
The nuclear magnetic data are as follows:
1H NMR(300MHz,CDCl3)δ＝7.79(d,J＝8.1Hz,2H),7.46-7.43(t,J＝7.5Hz,1H),7.34(s,1H),7.27-7.19(m,3H),6.88-6.81(t,2H),5.36(s,1H),3.80(s,3H),3.71(s,3H)。
compared with the existing synthesis method, the invention has the beneficial effects that:
1) according to the invention, indole derivatives and 3-phenyl trifluoromethyl acetone are used as raw materials, a series of 3-phenyl-3-indole trifluoromethyl acetone derivatives are efficiently synthesized under the catalysis of cuprous chloride, and the yield is considerable;
2) the compound contains an indole skeleton and a trifluoromethyl functional group, can be used as an organic synthesis intermediate, has the advantages of good group tolerance, wide substrate expansion range and the like, can be widely used in the fields of pesticides, medicines and the like, and provides an effective fragment for the synthesis of novel medicines;
3) the invention adopts catalytic amount of cuprous chloride to promote the synthesis of the 3-phenyl-3-indole trifluoromethyl acetone derivative, thereby greatly improving the product yield and shortening the reaction time.
The method has wide application in the fields of medicines, pesticides, chemical industry, organic synthesis and the like, and has the advantages of simple operation, mild reaction conditions, low cost, high yield and better application prospect.
The above embodiments are merely preferred embodiments, and all methods or common equivalent substitutions and modifications are within the scope of the present invention.
Claims (1)
1. A synthetic method of 3-phenyl-3-indole trifluoromethyl propyl ketone derivatives mainly comprises the following synthetic steps:
1) adding indole derivatives, 3-phenyl trifluoromethyl acetone, cuprous chloride and 1, 2-dichloroethane into a reaction tube, and reacting for 4 hours at 80 ℃ under the air atmosphere by magnetic stirring; wherein the mol ratio of the indole derivative to the 3-phenyl trifluoromethyl acetone is as follows: 3: 2;
2) after the reaction is finished, extracting with ethyl acetate, combining organic phases, distilling under reduced pressure to remove most of solvent to obtain a crude product, and performing column chromatography separation and purification on the crude product by taking a mixed solution of petroleum ether and ethyl acetate as an eluent to obtain a target product; wherein the volume ratio of the petroleum ether to the ethyl acetate is 10: 1;
the reaction equation is:
R1is methoxy, chlorine, fluorine; r2Is methyl, hydrogen.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103848774A (en) * | 2014-04-03 | 2014-06-11 | 辽宁科技大学 | Synthetic method of indolyl 1,2-ethanedione derivative |
| WO2016029310A1 (en) * | 2014-08-27 | 2016-03-03 | The Governing Council Of The University Of Toronto | Cannabinoid type 1 receptor modulators |
| CN106946758A (en) * | 2017-03-07 | 2017-07-14 | 丽水学院 | A kind of synthetic method of 3 (trifluoroacetyl) indole derivativeses |
| CN107417593A (en) * | 2017-04-12 | 2017-12-01 | 丽水学院 | A kind of synthetic method of 3,3,3 trifluoro 2 (3 ' indyl) 2 hydroxypropionates |
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- 2019-05-07 CN CN201910377169.1A patent/CN110028438B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103848774A (en) * | 2014-04-03 | 2014-06-11 | 辽宁科技大学 | Synthetic method of indolyl 1,2-ethanedione derivative |
| WO2016029310A1 (en) * | 2014-08-27 | 2016-03-03 | The Governing Council Of The University Of Toronto | Cannabinoid type 1 receptor modulators |
| CN106946758A (en) * | 2017-03-07 | 2017-07-14 | 丽水学院 | A kind of synthetic method of 3 (trifluoroacetyl) indole derivativeses |
| CN107417593A (en) * | 2017-04-12 | 2017-12-01 | 丽水学院 | A kind of synthetic method of 3,3,3 trifluoro 2 (3 ' indyl) 2 hydroxypropionates |
Non-Patent Citations (1)
| Title |
|---|
| "Copper(I) Chloride-Catalyzed Aerobic Oxidative Arylation of Glycine Ester and Amide Derivatives;Congde Huo et al.;《Adv. Synth. Catal.》;20140131;第356卷;第411-415页 * |
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