CN110668943A - Simple synthesis method of palladium metal catalyzed polysubstituted aryl ketone compound - Google Patents
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Abstract
The invention specifically designs a simple method for synthesizing a polysubstituted aryl ketone compound under the catalysis of palladium metal, belonging to the technical field of organic compound process application. As is well known, aryl ketone structures are widely existed in molecular structures of many clinical drugs, and the introduction of the aryl ketone structures into small molecules is one of important strategies for modifying the molecular structures of the drugs. The structure of the aryl ketone is relatively stable, and the introduction of the aryl ketone structure can improve the metabolic stability of the medicament by blocking metabolic sites, prolong the action time of the medicament and improve the bioavailability of the medicament.
Description
Technical Field
A simple method for synthesizing polysubstituted aryl ketone compound catalyzed by palladium metal belongs to the technical field of organic compound process application.
Background
Methods for synthesizing aryl ketone compounds have been reported. For example, the commonly used Friedel-crafts acylation reaction, under the action of Lewis acid, the hydrogen atom on the aromatic ring is replaced by acyl to finally generate aromatic ketone. But the raw materials of the Friedel-crafts acylation reaction require that an aromatic ring is provided with an electron-donating group, such as methyl, methoxy and the like; the difficulty of the reaction is increased by the aromatic ring substituted by the electron-withdrawing group. In general, the method has narrow substrate range and harsh reaction conditions. Aromatic ketones are widely used in pharmaceuticals, agrochemicals and polymers, and are also frequently used as dyes and photosensitizers, and have extremely high application values. In addition, the carbonyl compound can be converted into a compound containing a benzyl functional group through a series of reactions, and the next chemical reaction can be carried out. The aryl ketone compound is an important bioactive molecule, can improve the metabolic stability of the biomolecule, is an important drug molecule and a synthetic natural product intermediate, and has very high application value and research significance. Free phenol OXi8008 is a strong inhibitor of tubulin assembly as shown in the following figure, and may further synthesize anti-cancer drugs. The novel backbone of the novel polymer Rubialatins B can alter the biological activity of the molecule as shown in figure 1.
Disclosure of Invention
The invention overcomes the defects of the prior art, firstly proposes that active ester generated by Dicyclohexylcarbodiimide (DCC) and aryl carboxylic acid is used as electrophilic reagent of the Catellari reaction to react with aryl iodide, and synthesizes a series of polysubstituted aryl ketone compounds simply, conveniently and efficiently.
As shown in the figure (figure 2), the invention utilizes aryl iodide, aryl carboxylic acid and ketene compound as starting materials to react in a reaction solvent under the action of a metal palladium catalyst to synthesize an aryl ketone compound.
Wherein Ar is an aryl group.
In the invention, the dosage ratio of the starting materials 1, 2 and 3 is 1:4: 1.5.
In the present invention, the catalyst is allyl palladium chloride dimer or palladium acetate.
Preferably, the catalyst is allylpalladium chloride dimer.
In the invention, the ligand is trifurylphosphine hydrogen.
In the present invention, the base is Cs2CO3。
In the invention, the additive is DCC.
The solvent in the present invention is toluene. Wherein the solvent is used in an amount of 2 ml.
In the present invention, the reaction temperature is 90 DEGoC。
In the present invention, the reaction time is 10 hours.
Specifically, the synthesis method comprises the steps of adding reactant 2(0.2mmol), catalyst (5 mol%), ligand (10 mol%), alkali (0.6 mmol) into a 25ml Schlenk reaction tube, vacuumizing and exchanging nitrogen for three times, adding reactant 1, reactant 3, additive DCC, norbornene and solvent toluene, and reacting at 90 DEG CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction is finished, directly adding silica gel, spin-drying, performing column chromatography, and separating to obtain a pure target product 4.
The advantages of the synthetic product of the invention include: the raw materials used in the synthesis method are cheap and easy to obtain, the properties are very stable, and a special method is not needed for storage. The catalyst and the ligand used in the invention are common commercial reagents, are very stable, and have the characteristics of low cost, high yield, simple process and less pollution.
The synthesis method of aryl ketone compounds is a very potential method for modifying bioactive molecules, and the reaction route designed by the innovation of the invention provides a widely applicable synthesis method for modifying the compounds.
According to the invention, a novel electrophile is used for the first time in the Catellari reaction. The electrophile is an active ester intermediate formed by DCC and an aryl carboxylic acid.
According to the invention, aryl iodide and carboxylic acid are used as reaction substrates and react to obtain an aryl ketone compound. Simple reaction operation, mild reaction condition, high yield and large-scale production.
Drawings
FIG. 1 is a drawing of a drug and a biologically active molecule containing an aryl ketone structure.
FIG. 2 is a reaction formula of the synthesis method.
FIG. 3 is a reaction scheme using allylpalladium (II) chloride dimer as a catalyst.
FIG. 4 is a reaction scheme using palladium acetate as a catalyst.
FIG. 5 is a reaction scheme of 2-iodocumene with benzoic acid and butyl acrylate.
FIG. 6 is a reaction scheme of 1-iodonaphthalene with benzoic acid and butyl acrylate.
FIG. 7 is a reaction scheme of 2-iodotoluene with p-methylbenzoic acid and butyl acrylate.
FIG. 8 is a reaction scheme of 2-iodotoluene with p-chlorobenzoic acid and butyl acrylate.
FIG. 9 is a reaction scheme of 2-iodotoluene with m-acetylbenzoic acid, butyl acrylate.
FIG. 10 is a reaction scheme of 2-iodotoluene with benzoic acid, 1-penten-3-one.
FIG. 11 is a reaction scheme of 2-iodotoluene with benzoic acid and ethyl acrylate.
Detailed Description
The present invention will be described in further detail with reference to the following specific examples, but the present invention is not limited to the following examples. Variations and advantages that may occur to those skilled in the art may be incorporated into the invention without departing from the spirit and scope of the inventive concept, and the scope of the appended claims is intended to be protected. The procedures, conditions, reagents, experimental methods and the like for carrying out the present invention are general knowledge and common general knowledge in the art except for the contents specifically mentioned below, and the present invention is not particularly limited. The data given in the examples below include specific operating and reaction conditions and products. The product structure is determined by nuclear magnetic resonance (1H NMR，19F NMR，13C NMR) and HRMS identification.
Example 1 butyl (E) -3- (2-benzoyl-6-methylphenyl) acrylate (FIG. 3).
To a 25ml Schlenk reaction tube, reactant 2a (0.8mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1a (0.2mmol, 1.0equiv.), reactant 3a (1.5 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoC lower reactionShould be 10 hours. TLC monitored the progress of the reaction. After the reaction was complete, silica gel was added directly, and the pure target product 4a (53.5 mg, 83%) was isolated by spin-drying and column chromatography.1H NMR (400 MHz,CDCl3): δ 7.30-7.69 (m, 3H), 7.54 (t,J =7.2 Hz, 1H), 7.40 (t,J =7.6 Hz,2H), 7.34 (t,J =7.2 Hz, 2H), 7.27 (d,J =6.8 Hz, 1H), 5.88 (d,J =16 Hz,1H), 4.06 (t,J =6.4 Hz, 2H), 2.42 (s, 3H), 1.61-1.53 (m, 2H), 1.37-1.27 (m,2H), 0.91 (t,J =7.6Hz, 3H).13C NMR (100 MHz, CDCl3):δ 198.4, 165.9, 141.6,139.5, 137.5, 137.5, 133.2, 133.2, 132.1, 129.8, 128.4, 128.3, 126.4, 125.0,64.3, 30.5, 20.5, 19.0, 13.7.HRMS(ESI) calcd forC21H22O3Na [M+Na]+345.1467,found 345.1465。
Example 2 butyl (E) -3- (2-benzoyl-6-methylphenyl) acrylate (FIG. 4).
To a 25ml Schlenk reaction tube, reactant 2a (0.8mmol), catalyst Pd (OAc)2(5 mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1a (0.2mmol, 1.0equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction was complete, silica gel was added directly, spin-dried and column chromatographed to isolate the pure target 4a (50.2 mg, 78%). The analytical data were as in example 1.
Example 3 butyl (E) -3- (2-benzoyl-6-isopropylphenyl) acrylate (FIG. 5).
To a 25ml Schlenk reaction tube, reactant 2a (0.8mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1b (0.2mmol, 1.0equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction is finished, the reaction kettle is used for reaction,directly adding silica gel, spin-drying, and performing column chromatography to obtain pure target product 4b (63%).1H NMR (400 MHz, CDCl3): δ7.740 (d,J= 16 Hz, 1H), 7.62 (d,J= 7.6 Hz, 2H), 7.46 (t,J= 7.6 Hz, 1H),7.40 (d,J= 7.6 Hz, 1H), 7.34 (q,J= 6.8 Hz, 3H), 7.20 (d,J= 7.6 Hz, 1H),5.75 (d,J= 16.4 Hz, 1H), 3.98 (t,J= 6.8 Hz, 2H), 3.15-3.08 (m, 1H), 1.53-1.46 (m, 2H), 1.29-1.17 (m, 9H), 0.84 (t,J= 7.2 Hz, 3H).13C NMR (100 MHz,CDCl3): δ 198.5, 165.7, 147.8, 142.1, 139.5, 137.7, 133.1, 132.4, 129.7,128.5, 128.4, 127.1, 126.2, 125.5, 64.3, 30.5, 29.8, 23.5, 19.0, 13.7.HRMS(ESI) calcd forC23H26O3Na [M+Na]+373.1780, found 373.1773。
Example 4 butyl (E) -3- (2-benzoylnaphthalen-1-yl) acrylate (FIG. 6).
To a 25ml Schlenk reaction tube, reactant 2a (0.8mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1c (0.2mmol, 1.0equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction was complete, silica gel was added directly, spin-dried and column chromatographed to isolate the pure desired product 4c (49.1 mg, 69%).1H NMR (400 MHz,CDCl3): δ 8.15-8.10 (m, 2H), 7.94 (d,J= 8.8 Hz, 2H), 7.73 (d,J= 7.6 Hz,2H), 7.62 (q,J= 3.2 Hz, 2H), 7.57-7.52 (m, 2H), 7.41 (t,J= 7.6 Hz, 2H),6.09 (d,J= 16.4 Hz, 1H), 4.11 (t,J= 6.4 Hz, 2H), 1.64-1.57 (m, 2H), 1.39-1.30 (m, 2H), 0.93 (t,J= 7.2 Hz, 3H).13C NMR (100 MHz, CDCl3): δ 198.4,165.4,140.9, 137.6, 136.6, 133.9, 133.3, 132.0 131.0, 129.8, 129.0, 128.6,128.5, 127.5, 127.4, 126.8, 125.3, 125.0, 64.5, 30.6, 19.1, 13.7.HRMS(ESI)calcd forC24H22O3Na [M+Na]+381.1467, found 381.1465。
Example 5 butyl (E) -3- (2-methyl-6- (4-methylbenzoyl) phenyl) acrylate (FIG. 7).
To a 25ml Schlenk reaction tube, reaction 2b (0.8mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1a (0.2mmol, 1.0equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction was completed, silica gel was directly added, and by spin-drying and column chromatography, the pure target product 4d (46.5 mg, 72%) was isolated.1H NMR (400 MHz,CDCl3): δ 7.71 (d,J= 16 Hz, 1H ), 7.61 (d,J= 8 Hz, 2H), 7.35-7.30 (m,2H), 7.24 (d,J= 6.8 Hz, 1H), 7.20 (d,J= 8Hz, 2H), 5.89 (d,J= 16 Hz,1H), 4.06 (t,J= 6.4 Hz, 2H), 2.40 (d,J= 7.2 Hz, 6H), 1.60-1.53 (m, 2H),1.37-1.27 (m, 2H), 0.91 (t,J= 7.2 Hz, 3H).13C NMR (100 MHz, CDCl3): δ198.0, 166.0, 144.1, 141.6, 139.9, 137.5, 134.9, 133.0, 131.9, 130.0, 129.2,128.2, 126.2, 124.9, 64.3, 30.5, 21.7, 20.5, 19.0, 13.7.HRMS(ESI) calcdforC22H24O3Na [M+Na]+359.1623, found 359.1622。
Example 6 butyl (E) -3- (2- (4-chlorobenzoyl) -6-methylphenyl) acrylate (FIG. 8).
To a 25ml Schlenk reaction tube, reaction 2C (0.8mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1a (0.2mmol, 1.0equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction is finished, directly adding silica gel, spin-drying, passing through column chromatography, and separating to obtain pure target product 4e (47.6 m)g, 65%)。1H NMR (400 MHz,CDCl3): δ 7.74-7.68 (m, 3H), 7.33-7.29 (m, 2H), 7.22 (dd,J 1 =8.0 Hz,J 2 =2Hz, 2H), 6.87 (d,J= 8.8 Hz, 2H), 5.90 (d,J= 16 Hz, 1H), 4.06 (t,J= 6.4Hz, 2H), 3.85 (s, 3H), 2.41 (s, 3H), 1.61-1.54 (m, 2H), 1.36-1.27 (m, 2H),0.90 (t,J= 7.6 Hz, 3H).13C NMR (100 MHz, CDCl3): δ 197.0, 166.1, 163.7,141.5, 140.0, 137.5, 132.8, 132.3, 131.8, 130.3, 128.3, 126.0, 124.8, 113.7,64.3, 55.5, 30.6, 20.5, 19.1, 13.7. HRMS(ESI) calcd forC21H21ClO3Na [M+Na]+379.1077, found 379.1076。
Example 7 butyl (E) -3- (2- (3-acetylbenzoyl) -6-methylphenyl) acrylate (fig. 9).
To a 25ml Schlenk reaction tube, reaction 2d (0.2mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1a (0.2mmol, 1.0equiv.), reactant 3a (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction was complete, silica gel was added directly, spin-dried and column chromatographed to isolate the pure desired product 4f (57 mg, 82%).1H NMR (400 MHz,CDCl3): δ 8.30(s,1H), 8.14 (d,J= 7.6 Hz, 1H), 7.86 (d,J= 8 Hz, 1H), 7.71(d,J= 16 Hz, 1H), 7.52 (t,J= 7.6 Hz, 1H), 7.41-7.35 (m, 2H), 7.29-7.27 (m,1H), 5.86 (d,J= 16.4 Hz,1H), 4.06 (t,J= 6.4 Hz, 2H), 2.62 (s, 3H), 2.43(s, 3H), 1.60-1.53 (m, 2H), 1.36-1.26 (m,2H), 0.90 (t,J= 7.2 Hz, 3H).13C NMR(100 MHz, CDCl3): δ 197.5, 197.1, 165.8, 141.6, 138.9, 138.0, 137.8, 137.3,134.1, 133.4, 132.7, 132.5, 129.3, 128.9, 128.5, 126.5, 125.3, 64.4, 30.5,26.7, 20.4, 19.1, 13.7. HRMS(ESI) calcd forC23H24O4Na [M+Na]+387.1573, found387.1576。
Example 8, (E) -1- (2-benzoyl-6-isopropylphenyl) pent-1-en-3-one (FIG. 10).
To a 25ml Schlenk reaction tube, reaction 2a (0.8mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1a (0.2mmol, 1.0equiv.), reactant 3b (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction is finished, silica gel is directly added, and the pure target product 4g (61.2 mg, 95%) is obtained by spin-drying and column chromatography.1H NMR (400 MHz,CDCl3): δ 7.71 (d,J= 7.6 Hz, 2H), 7.60 (d,J= 16.4 Hz, 1H), 7.54 (t,J=7.2 Hz, 1H), 7.41 (t,J= 7.6 Hz, 2H), 7.38-7.33 (m, 2H), 7.28 (dd,J 1 = 6.8Hz,J 2 = 2, 1H), 6.15 (d,J= 16.4 Hz, 1H), 2.45-2.39 (m, 5H), 0.98 (t,J=7.2 Hz, 3H).13C NMR (100 MHz, CDCl3): δ 200.0, 198.4, 139.4, 139.2, 137.6,137.5, 133.5, 133.3, 132.5, 132.2, 129.7, 128.5, 128.3, 126.5, 34.0, 20.4,7.9.HRMS(ESI) calcd forC19H18O2Na [M+Na]+301.1205, found 301.1217。
Example 9 ethyl (E) -3- (2-benzoyl-6-methylphenyl) acrylate (fig. 11).
To a 25ml Schlenk reaction tube, reactant 2a (0.8mmol), catalyst [ PdCl (C)3H5)]2(2.5mol%), ligand TFP (10 mol%), alkali Cs2CO3(0.6 mmol), vacuum-pumping and nitrogen-exchanging three times, adding reactant 1a (0.2mmol, 1.0equiv.), reactant 3c (0.3 mmol), additive DCC (0.9 mmol), norbornene (0.5 mmol) and solvent toluene (2mL), reacting at 90 deg.CoAnd C, reacting for 10 hours. TLC monitored the progress of the reaction. After the reaction is finished, silica gel is directly added, and the pure target product is obtained by separation after spin-drying and column chromatography for 4h (54.7 mg, 93%).1H NMR (400 MHz,CDCl3): δ 7.73 (t,J= 8 Hz, 3H), 7.55 (t,J= 7.2 Hz, 1H), 7.41 (t,J= 7.6Hz, 2H), 7.37-7.31 (m, 2H), 7.26 (d,J= 6 Hz, 1H), 5.88 (d,J= 16 Hz, 1H),4.12 (q,J= 7.2 Hz, 2H), 2.42 (s, 3H), 1.22 (t,J= 7.2 Hz, 3H).13C NMR (100MHz, CDCl3): δ 198.3, 165.8, 141.7, 139.5, 137.5, 137.5, 133.3, 133.2, 132.2,129.8, 128.4, 128.2, 126.4, 125.0, 60.4, 20.5, 14.1. HRMS(ESI) calcdforC19H18O3Na [M+Na]+317.1154, found 317.1160。
Claims (9)
1. A method for synthesizing palladium metal catalyzed polysubstituted aryl ketone compounds is characterized in that aryl iodides, benzoic acid, DCC and butyl acrylate are used as raw materials, and are reacted in a reaction solvent through multi-step series reaction under the action of a palladium catalyst to obtain acylation products of the aryl iodides, wherein the reaction equation is shown as the following formula:
wherein Ar is an aryl group.
2. The method of synthesizing a palladium metal catalyzed poly-substituted aryl ketone compound of claim 1 wherein the catalyst is allylpalladium (II) chloride dimer or palladium acetate.
3. The palladium metal catalyzed process for synthesizing a poly-substituted aryl ketone compound as claimed in claim 1, wherein the ligand is tris (2-furyl) phosphine.
4. The method of synthesizing a palladium metal catalyzed polysubstituted aryl ketone compound of claim 1 wherein said base is Cs2CO3。
5. The method for synthesizing a palladium metal catalyzed polysubstituted aryl ketone compound according to claim 1, wherein said additive is DCC.
6. The palladium metal catalyzed process for synthesizing a polysubstituted aryl ketone compound according to claim 1, wherein said solvent is toluene.
7. Wherein the solvent is used in an amount of 2 ml.
8. The method of synthesizing a palladium metal catalyzed polysubstituted aryl ketone compound according to claim 1, wherein said reaction temperature is 90 deg.foC。
9. The palladium metal catalyzed process for synthesizing a polysubstituted aryl ketone compound according to claim 1, wherein said reaction time is 10 hours.
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