CN102432523A - Method for synthesizing 3-hydroxy-3-arylindole-2-one derivative - Google Patents
Method for synthesizing 3-hydroxy-3-arylindole-2-one derivative Download PDFInfo
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Abstract
The invention discloses a method for synthesizing a 3-hydroxy-3-arylindole-2-one derivative shown as a structural formula (I), which comprises the following steps of: fully reacting raw materials such as an isatin compound shown as a structural formula (II) and arylboric acid shown as a structural formula (III) in an inert organic solvent in the presence of a copper catalyst, a nitrogen-containing bidentate ligand and an alkaline compound, and separating and purifying reaction liquid after the reaction is finished to obtain the 3-hydroxy-3-arylindole-2-one derivative, wherein the copper catalyst is one or any combination of copper trifluoromethanesulfonate, copper acetylacetonate, copper acetate, cuprous iodide, copper bromide, copper fluoride and copper chloride. The method is high in implementation value and good in social benefit and economic benefit.
Description
(1) technical field
The present invention relates to the chemical synthesis process of a kind of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives.
(2) background technology
3-hydroxyl-3-(hetero) aryl indole-2-ketone compounds is one type of compound with good biological activity and pharmacologically active; Be widely used in the synthetic of agricultural chemicals, medicine; Have very high practical value, its verivate is being brought into play active effect at aspects such as anticancer, anti-inflammatory, treatment hematologic diseases.
In the prior art; (as: the Angew.Chem.Int.Ed.2011 that has; 50,7620) synthesize 3-hydroxyl-3-(hetero) aryl indole-2-one derivative compounds with intramolecular cyclization reaction, this method is to utilize metal palladium catalyst to be configured to ring structure; To the strict of the structure of reaction substrate and be difficult to obtain, and catalyst system therefor is relatively more expensive.Have (like J.Am.Chem.Soc.2004; 126,12888 and Bioorg.Med.Chem.Lett.2010,20; 3103) synthesize 3-hydroxyl-3-(hetero) aryl indole-2-ketone compounds with organometallic reagent (like Grignard reagent or organolithium reagent) as aromatic yl reagent-ing; This method is a nucleophilicity of utilizing organometallic reagent stronger, but because the toxicity of organometallic reagent and to the restriction of functional group, and the shortcomings such as sensitivity of empty G&W are all being limited being widely used of this method.
To the above unfavorable factor of considering, therefore existing method is improved, develop a kind of efficient, cheapness, 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives compound method has very big economic benefit and social benefit easily.
(3) summary of the invention
The purpose of this invention is to provide a kind of technology rationally, hypotoxicity, reaction conditions is gentle, reaction yield is high and the chemical synthesis process of the 3-of good product quality hydroxyl-3-(hetero) aryl indole-2-ketone derivatives.
For realizing the foregoing invention purpose, the present invention adopts following technical scheme:
A kind of structure is suc as formula the compound method of the 3-hydroxyl shown in (I)-3-(hetero) aryl indole-2-ketone derivatives; Said method comprises the following steps: that be raw material suc as formula isatin compounds shown in (II) and structure suc as formula the aryl boric acid shown in (III) with structure; Fully reaction in inert organic solvents in the presence of copper catalyst, nitrogenous bitooth ligand and basic cpd, reaction finishes afterreaction liquid and obtains described 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives through separation and purification; Described copper catalyst is selected from following a kind of or any several kinds combination: copper trifluoromethanesulfcomposite, acetylacetone copper, neutralized verdigris, cuprous iodide, cupric bromide, cupric fluoride, cupric chloride;
Formula (I), (II) or (III) in, R
1And R
2Independently be selected from one of following separately: the alkyl of hydrogen, C1～C8, the alkoxyl group of C1～C8, allyl group, benzyl, hydrocinnamyl, halogen; R
3Be selected from one of following: phenyl, naphthyl, substituted-phenyl, the substituting group of said substituted-phenyl are the alkyl of C1～C8, alkoxyl group, trifluoromethyl, halogen, nitro or the phenyl of C1～C8.
Further, described R
1Be preferably one of following: the alkyl of hydrogen, C1～C8, C1～C8 alkoxyl group, halogen, one of more preferably following: hydrogen, methyl, methoxyl group, halogen further are preferably one of following: hydrogen, methyl, methoxyl group, chlorine.
Further, described R
2One of be preferably one of following: the alkyl of C1～C8, allyl group, benzyl, hydrocinnamyl, more preferably following: methyl, normal-butyl, n-hexyl, allyl group, benzyl, hydrocinnamyl.
Further, described R
3Be preferably one of following: phenyl, substituted-phenyl, the substituting group of said substituted-phenyl are selected from one of following: the alkyl of C1～C8, the alkoxyl group of C1～C8, trifluoromethyl, halogen, nitro or phenyl; The alkyl of described C1～C8 is preferably methyl, and the alkoxyl group of described C1～C8 is preferably methoxyl group.
It is one of following that nitrogenous bitooth ligand of the present invention can be selected from: a water phenanthroline, 4,7-dimethyl-phenanthroline, dipyridyl, 4,4 '-dimethyl--2,2 '-dipyridyl; Be preferably a water phenanthroline.
Basic cpd of the present invention can be like mineral alkalis such as yellow soda ash, salt of wormwood, cesium carbonate, Quilonum Retard, sodium hydroxide, Pottasium Hydroxide, Lithium Hydroxide MonoHydrate, potassiumphosphate, Potassium monofluoride, Repone K, lithium fluoride, lithiumbromide, sodium-acetate, potassium tert.-butoxides; Also can be organic basess such as triethylamine, urotropine; It also can be the mixture of above-mentioned mineral alkali and organic bases.
The organic solvent of inert organic solvents according to the invention for not reacting with reactant; Usually can select alkanes, halogenated hydrocarbon, the N of C1～C8 for use; N, a kind of or any several kinds combination in-dimethylformamide class, ester class, alcohols, ethers, ketone, the nitrile solvents, preferred methylene dichloride.The quality consumption of said inert organic solvents is 1～35 times of said isatin compounds quality, is preferably 15～25 times.
Copper catalyst of the present invention is preferably copper trifluoromethanesulfcomposite or acetylacetone copper.
The molar ratio of isatin compounds according to the invention and aryl boric acid, mantoquita, nitrogenous bitooth ligand and basic cpd is 1.0: 1.0～6.0: 0.01～1.0: 0.01～1.0: 1.0～5.0; Be preferably 1.0: 2.0～4.0: 0.05～0.1: 0.05～0.1: 2.0～3.5, more preferably 1.0: 3.0～4.0: 0.05～0.1: 0.05～0.1: 2.5～3.5.
Among the present invention, temperature of reaction is 30～150 ℃, is preferably 45～100 ℃; Reaction times is preferably 24～48h generally at 5～72h.
Separation and purification of the present invention can be adopted following method: the gained reaction solution steams earlier and desolventizes; Add saturated sodium bicarbonate again, separate and get organic layer, the rotation evaporate to dryness; Bullion is used ethyl alcohol recrystallization, is described 3-hydroxyl-3-Phenylindole-2-ketone derivatives after the drying.
The concrete chemical synthesis process of described 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives of recommending of the present invention carries out according to following steps: under the room temperature, be that 1.0: 3.0～4.0: 0.05～0.1: 0.05～0.1: 2.5～3.5 isatin compounds, aryl boric acid, copper catalyst, nitrogenous bitooth ligand and basic cpd add in the reaction kettle with mol ratio, after the inert organic solvents dissolving; Be warming up to 30-150 ℃; Reaction 5h-72h is to reacting completely, and steaming earlier desolventizes, and adds saturated sodium bicarbonate again; Separate and get organic layer; The rotation evaporate to dryness, bullion is used ethyl alcohol recrystallization, is described 3-hydroxyl-3-Phenylindole-2-ketone derivatives after the drying.
The present invention compared with prior art, its beneficial effect is mainly reflected in: 1. reaction yield is higher relatively, good product quality; 2. operational path is advanced rationally, reaction conditions is gentle; 3. the few and low price of catalyst levels; So the present invention has bigger implementary value and economic results in society.
(4) embodiment
Below in conjunction with specific embodiment the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1:
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 2.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 24.4g (0.2mol); Copper trifluoromethanesulfcomposite 1.8g (0.005mol); One water phenanthroline 2.0g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is YLENE 241.5g, and its total consumption is 15 times of N-methyl-isatin quality.
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are dropped in the reaction kettle, add xylene soluble, temperature of reaction is 100 ℃, and afterreaction finished in 48 hours.
Reaction finishes the back underpressure distillation and reclaims organic solvent, and the solid that remains in the reaction flask gets white solid through the ethyl alcohol recrystallization of crossing with the calcium chloride drying, promptly gets N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 14.8g, yield 62%, purity 98.1%.
Nuclear magnetic resonance spectrum (Bruke):
1H NMR (CDCl
3, 500MHz): δ (ppm)=3.17 (3H, s), 3.40 (1H, s), 6.83 (1H, d, J=10Hz), 7.02 (1H, t, J=10Hz), 7.18-7.32 (7H, m);
13C NMR (CDCl
3, 125MHz): δ (ppm)=26.5,77.9,108.7,123.5,124.9,125.3,128.3,128.6,129.9,131.6,140.1,143.5,177.5.
Embodiment 2:
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, 4,4 '-dimethyl--2,2 '-dipyridyl, Lithium Hydroxide Monohydrate are 1.0: 2.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 24.4g (0.2mol); Copper trifluoromethanesulfcomposite 0.92g (0.005mol); 4,4 '-dimethyl--2,2 '-dipyridyl 2.08g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is YLENE 241.5g, and its total consumption is 15 times of N-methyl-isatin quality.
All the other are with embodiment 1, products obtained therefrom N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 11.9g, yield 50%, purity 98.5%.
Embodiment 3:
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, cesium carbonate are 1.0: 2.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 24.4g (0.2mol); Copper trifluoromethanesulfcomposite 1.8g (0.005mol); One water phenanthroline 2.0g (0.01mol); Cesium carbonate 97.8g (0.3mol); Organic solvent is YLENE 241.5g, and its total consumption is 15 times of N-methyl-isatin quality.
All the other are with embodiment 1, products obtained therefrom N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 13.9g, yield 58%, purity 98.4%.
Embodiment 4:
N-methyl-isatin, phenylo boric acid, cuprous iodide, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 2.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 24.4g (0.2mol); Cuprous iodide 0.95g (0.005mol); One water phenanthroline 2.0g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is YLENE 241.5g, and its total consumption is 15 times of N-methyl-isatin quality.
All the other are with embodiment 1, products obtained therefrom N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 13.6g, yield 57%, purity 97.9%.
Embodiment 5:
N-methyl-isatin, phenylo boric acid, cupric bromide, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 2.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 24.4g (0.2mol); Copper trifluoromethanesulfcomposite 1.8g (0.005mol); One water phenanthroline 2.0g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is toluene 241.5g, and its total consumption is 15 times of N-methyl-isatin quality.
All the other are with embodiment 1, products obtained therefrom N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 13.9g, yield 58%, purity 99.2%.
Embodiment 6:
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 2.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 24.4g (0.2mol); Copper trifluoromethanesulfcomposite 1.8g (0.005mol); One water phenanthroline 2.0g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is methylene dichloride 241.5g, and its total consumption is 15 times of N-methyl-isatin quality.
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are dropped in the reaction kettle, add methylene dichloride dissolving back sealing.Temperature of reaction is 80 ℃, and 48 hours finish.
Reaction finishes the back underpressure distillation and reclaims organic solvent, and the solid that remains in the reaction flask gets white solid through the ethyl alcohol recrystallization of crossing with the calcium chloride drying, promptly gets N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 17.1g, yield 71%, purity 99%.
Embodiment 7:
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 2.0: 0.1 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 24.4g (0.2mol); Copper trifluoromethanesulfcomposite 3.6g (0.01mol); One water phenanthroline 2.0g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is methylene dichloride 322g, and its total consumption is 20 times of N-methyl-isatin quality.
All the other are with embodiment 6, products obtained therefrom N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 19.6g, yield 82%, purity 98.8%.
Embodiment 8:
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 3.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 36.6g (0.3mol); Copper trifluoromethanesulfcomposite 1.8g (0.005mol); One water phenanthroline 2.0g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is methylene dichloride 322g, and its total consumption is 20 times of N-methyl-isatin quality.
All the other are with embodiment 6, products obtained therefrom N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 20.6g, yield 86%, purity 99.2%.
Embodiment 9:
N-methyl-isatin, phenylo boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 4.0: 0.05 with the amount of substance ratio: feed intake N-methyl-isatin 16.1g (0.1mol) at 0.1: 3.0; Phenylo boric acid 48.8g (0.4mol); Copper trifluoromethanesulfcomposite 1.8g (0.005mol); One water phenanthroline 2.0g (0.01mol); Lithium Hydroxide Monohydrate 12.6g (0.3mol); Organic solvent is methylene dichloride 241.5g, and its total consumption is 15 times of N-methyl-isatin quality.
All the other are with embodiment 6, products obtained therefrom N-methyl-3-hydroxyl-3-Phenylindole-2-ketone 21.9g, yield 91%, purity 99.3%.
Embodiment 10～33:
Isatin, aryl boric acid, copper trifluoromethanesulfcomposite, a water phenanthroline, Lithium Hydroxide Monohydrate are 1.0: 4.0: 0.05 with the amount of substance ratio: the back that feeds intake added 80 ℃ of methylene dichloride heated sealed in 0.1: 3.0; Reacted 48 hours; All the other steps are with embodiment 6, and the result is as shown in the table:
Claims (10)
1. a structure is suc as formula the compound method of the 3-hydroxyl shown in (I)-3-(hetero) aryl indole-2-ketone derivatives; Said method comprises the following steps: that be raw material suc as formula isatin compounds shown in (II) and structure suc as formula the aryl boric acid shown in (III) with structure; Fully reaction in inert organic solvents in the presence of copper catalyst, nitrogenous bitooth ligand and basic cpd; Reaction finishes afterreaction liquid through separation and purification, obtains described 3-hydroxyl-3-Phenylindole-2-ketone derivatives; Described copper catalyst is selected from following a kind of or any several kinds combination: copper trifluoromethanesulfcomposite, acetylacetone copper, neutralized verdigris, cuprous iodide, cupric bromide, cupric fluoride, cupric chloride;
Formula (I), (II) or (III) in, R
1And R
2Independently be selected from one of following separately: the alkyl of hydrogen, C1～C8, the alkoxyl group of C1～C8, allyl group, benzyl, hydrocinnamyl, halogen; R
3Be selected from one of following: phenyl, naphthyl, substituted-phenyl, the substituting group of said substituted-phenyl are the alkyl of C1～C8, alkoxyl group, trifluoromethyl, halogen, nitro or the phenyl of C1～C8.
2. the compound method of 3-hydroxyl as claimed in claim 1-3-(hetero) aryl indole-2-ketone derivatives is characterized in that: described R
1For one of following: the alkyl of hydrogen, C1～C8, the alkoxyl group of C1～C8, halogen; Described R
2For one of following: the alkyl of C1～C8, allyl group, benzyl, hydrocinnamyl.
3. according to claim 1 or claim 2 the compound method of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives; It is characterized in that: described nitrogenous bitooth ligand is selected from one of following: a water phenanthroline, 4; 7-dimethyl-phenanthroline, dipyridyl, 4,4 '-dimethyl--2,2 '-dipyridyl.
4. according to claim 1 or claim 2 the compound method of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives, it is characterized in that: described basic cpd is selected from following a kind of or any several kinds combination: yellow soda ash, salt of wormwood, cesium carbonate, Quilonum Retard, sodium hydroxide, Pottasium Hydroxide, Lithium Hydroxide MonoHydrate, potassiumphosphate, Potassium monofluoride, Repone K, lithium fluoride, lithiumbromide, sodium-acetate, potassium tert.-butoxide, triethylamine, urotropine.
5. according to claim 1 or claim 2 the compound method of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives; It is characterized in that: said inert organic solvents is selected from following a kind of or any several kinds combination: the alkanes of C1～C8, halogenated hydrocarbon, N; N ,-dimethylformamide class, ester class, alcohols, ethers, ketone, nitrile solvents.
6. according to claim 1 or claim 2 the compound method of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives, it is characterized in that: described copper catalyst is copper trifluoromethanesulfcomposite or acetylacetone copper; Described nitrogenous bitooth ligand is a water phenanthroline; Described basic cpd is a Lithium Hydroxide Monohydrate; Described inert organic solvents is a methylene dichloride.
7. according to claim 1 or claim 2 the compound method of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives, it is characterized in that: the molar ratio of said isatin compounds and aryl boric acid, copper catalyst, nitrogenous bitooth ligand and basic cpd is 1.0: 1.0～6.0: 0.01～1.0: 0.01～1.0: 1.0～5.0; The quality consumption of said inert organic solvents is 1～35 times of said isatin compounds quality.
8. according to claim 1 or claim 2 the compound method of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives, it is characterized in that: the molar ratio of said isatin compounds, aryl boric acid, copper catalyst, nitrogenous bitooth ligand and basic cpd is 1.0: 2.0～4.0: 0.05～0.1: 0.05～0.1: 2.0～3.5; The quality consumption of said inert organic solvents is 15～25 times of said isatin compounds quality.
9. according to claim 1 or claim 2 the compound method of 3-hydroxyl-3-(hetero) aryl indole-2-ketone derivatives is characterized in that: said being reflected under 30～150 ℃ the temperature condition carried out.
10. the compound method of 3-hydroxyl as claimed in claim 9-3-(hetero) aryl indole-2-ketone derivatives is characterized in that: temperature of reaction is 45～100 ℃, and the reaction times is 24～48h.
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