CN110372694A - A kind of new method of 2- phenylimidazole [1,2-a] pyridine -3- aldehyde replaced using DMF as formylation reagent building - Google Patents
A kind of new method of 2- phenylimidazole [1,2-a] pyridine -3- aldehyde replaced using DMF as formylation reagent building Download PDFInfo
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- CN110372694A CN110372694A CN201910712813.6A CN201910712813A CN110372694A CN 110372694 A CN110372694 A CN 110372694A CN 201910712813 A CN201910712813 A CN 201910712813A CN 110372694 A CN110372694 A CN 110372694A
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- pyridine
- phenylimidazole
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- dimethylformamide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses one kind with the new method of 2- phenylimidazole [1,2-a] pyridine -3- aldehyde that DMF (N,N-dimethylformamide) is the building substitution of one step of formylation reagent.2- phenylimidazole [1,2-a] pyridine of this method to replace constructs 2- phenylimidazole [1, the 2-a] pyridine -3- aldehyde replaced using DMF (n,N-Dimethylformamide) as one step of formylation reagent as reaction raw materials.The method of the present invention synthesizing mean is novel, and reaction condition is mild, and reaction reagent is cheap and easy to get, and n,N-Dimethylformamide not only can be used as reaction dissolvent but also can be used as formylation reagent, meets the demand for development of Green Chemistry.
Description
Technical field
The invention belongs to the technical fields such as medicine, material, cell biology, and in particular to one kind with DMF (N, N- diformazan
Base formamide) it is the new method that one step of formylation reagent constructs 2- phenylimidazole [1,2-a] pyridine -3- aldehyde replaced.
Background technique
2- phenylimidazole [1,2-a] pyridine -3- aldehyde compound is a kind of very important pharmaceutical intermediate, can be used for closing
At the various drug molecules with pharmaceutical activity, the structural framework for being included using such compound can construct me as starting material
Known to drug molecule grains of sand pyrrole denier with antidepressant effect and have anesthesiophore Necopidem.It is with grains of sand pyrrole denier
Example: grains of sand pyrrole denier and benzodiazepine compounds seemingly, have calm and antidepressant effect.The chemical structure and benzene of grains of sand pyrrole denier
The architectural difference of two nitrogen compounds is larger, therefore is considered being non-benzodiazepine compound.Grains of sand pyrrole denier has good choosing
Selecting property plays calm and antidepressant pharmacological action by adjusting the binding site with GABAA.It can be seen that 2- phenylimidazole
The synthesis of [1,2-a] pyridine -3- aldehyde compound has important researching value in pharmaceutical synthesis field.It is carried on the back in such research
Under scape, it is that one step of formylation reagent constructs the 2- phenyl replaced that we have proposed one kind with DMF (n,N-Dimethylformamide)
The new method of imidazoles [1,2-a] pyridine -3- aldehyde, synthetic route are as follows:
Substituted 2- phenylimidazole [1,2-a] pyridine -3- aldehyde that the present invention synthesizes, structural formula are as follows:
The invention with DMF (N,N-dimethylformamide) be one step of formylation reagent building replace 2- phenylimidazole [1,
2-a] pyridine -3- aldehyde, a novel synthetic route is provided for the synthesis of such compound.The invention synthesizing mean is novel,
Reaction condition is mild, and reaction reagent is cheap and easy to get, and n,N-Dimethylformamide not only can be used as reaction dissolvent but also can be used as first
Acylating reagent meets the demand for development of Green Chemistry.
Summary of the invention
It is that one step of formylation reagent constructs the 2- phenyl replaced that the present invention relates to one kind with DMF (N,N-dimethylformamide)
The new method of imidazoles [1,2-a] pyridine -3- aldehyde.This method with 2- phenylimidazole [1, the 2-a] pyridine that replaces as reaction raw materials,
2- phenylimidazole [1,2-a] pyridine -3- that building replaces using DMF (N,N-dimethylformamide) as one step of formylation reagent
Aldehyde.The method of the present invention synthesizing mean is novel, and reaction condition is mild, and reaction reagent is cheap and easy to get, and n,N-Dimethylformamide both may be used
Can be used as formylation reagent again as reaction dissolvent, meet the demand for development of Green Chemistry.
Technical solution of the present invention is as follows.
One kind is with the 2- phenylimidazole [1,2- that DMF (N,N-dimethylformamide) is that the building of one step of formylation reagent replaces
A] pyridine -3- aldehyde new method, synthetic route is as follows:
In the above method, described substituted 2- phenylimidazole [1,2-a] pyridine -3- aldehyde is by compound 1 through formylation reaction
One step is made；The compound 1 is 2- phenylimidazole [1, the 2-a] pyridine replaced, the specific steps are as follows:
It takes compound 1 (substituted 2- phenylimidazole [1,2-a] pyridine) to be placed in container, promotor and solvent, set is added
On the balloon filled with oxygen gas, be stirred to react 1-48 hours, be cooled to room temperature after reaction, remove balloon, reaction solution mistake
It filters, after evaporating solvent under reduced pressure, obtains crude product, 2- phenylimidazole [1, the 2-a] pyridine -3- aldehyde replaced through column Chromatographic purification；
In the above method, the reaction vessel of the specific steps is teat glass；The promotor is Gerhardite；
The solvent is DMF (N,N-dimethylformamide).
The amount and (the substituted 2- phenylimidazole [1,2- of compound 1 of mantoquita are added in the above method, in the specific steps
A] pyridine) molar ratio be 0.5:1.
In the above method, the balloon pressure described in the specific steps filled with oxygen gas is 1 atmospheric pressure.
Compared with prior art, present invention has an advantage that this method synthesizing mean is novel, with DMF (N, N- dimethyl methyl
Amide) it is 2- phenylimidazole [1,2-a] pyridine -3- aldehyde that the building of one step of formylation reagent replaces, synthesizing mean is novel, reacts item
Part is mild, and reaction reagent is cheap and easy to get, and n,N-Dimethylformamide not only can be used as reaction dissolvent but also can be used as formylated examination
Agent meets the demand for development of Green Chemistry.
Detailed description of the invention
Fig. 1 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 1；
Fig. 2 is the carbon-13 nmr spectra of products therefrom in embodiment 1；
Fig. 3 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 2；
Fig. 4 is the carbon-13 nmr spectra of products therefrom in embodiment 2；
Fig. 5 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 3；
Fig. 6 is the carbon-13 nmr spectra of products therefrom in embodiment 3；
Fig. 7 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 4；
Fig. 8 is the carbon-13 nmr spectra of products therefrom in embodiment 4；
Fig. 9 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 5；
Figure 10 is the carbon-13 nmr spectra of products therefrom in embodiment 5；
Figure 11 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 6；
Figure 12 is the carbon-13 nmr spectra of products therefrom in embodiment 6；
Figure 13 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 7；
Figure 14 is the carbon-13 nmr spectra of products therefrom in embodiment 7；
Figure 15 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 8；
Figure 16 is the carbon-13 nmr spectra of products therefrom in embodiment 8；
Figure 17 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 9；
Figure 18 is the carbon-13 nmr spectra of products therefrom in embodiment 9；
Figure 19 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 10；
Figure 20 is the carbon-13 nmr spectra of products therefrom in embodiment 10；
Figure 21 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 11；
Figure 22 is the carbon-13 nmr spectra of products therefrom in embodiment 11；
Figure 23 is the nuclear magnetic resonance spectroscopy of products therefrom in embodiment 12；
Figure 24 is the carbon-13 nmr spectra of products therefrom in embodiment 12；
Specific embodiment
The invention is further described below by specific embodiment.
Embodiment 1
0.2 mM of pyridine of compound 7- methyl -2- phenylimidazole [1,2-a], three hydrations are added in the test tube of 25mL
0.1 mM of copper nitrate, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the gas filled with oxygen
Ball stirs under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes gas
Ball is slowly vented unreacted oxygen.Reaction solution filtering, filtrate decompression revolving removal solvent, then pass through column chromatographic isolation and purification,
Obtain compound 7- methyl -2- phenylimidazole [1,2-a] pyridine -3- aldehyde, the step yield 80%.
Embodiment 2
Fluoro- 0.2 mM of pyridine of 2- phenylimidazole [1,2-a] of compound 6- is added in the test tube of 25mL, three hydration nitre
0.1 mM of sour copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the balloon filled with oxygen,
It is stirred under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes balloon, is delayed
The empty unreacted oxygen of slow play.Reaction solution filtering, filtrate decompression revolving removal solvent, then by column chromatographic isolation and purification, obtain
Fluoro- 2- phenylimidazole [1, the 2-a] pyridine -3- aldehyde of compound 6-, the step yield 65%.
Embodiment 3
Chloro- 0.2 mM of pyridine of 2- phenylimidazole [1,2-a] of compound 6- is added in the test tube of 25mL, three hydration nitre
0.1 mM of sour copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the balloon filled with oxygen,
It is stirred under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes balloon, is delayed
The empty unreacted oxygen of slow play.Reaction solution filtering, filtrate decompression revolving removal solvent, then by column chromatographic isolation and purification, obtain
Chloro- 2- phenylimidazole [1, the 2-a] pyridine -3- aldehyde of compound 6-, the step yield 68%.
Embodiment 4
0.2 mM of pyridine of compound 6- phenyl -2- phenylimidazole [1,2-a], three hydrations are added in the test tube of 25mL
0.1 mM of copper nitrate, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the gas filled with oxygen
Ball stirs under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes gas
Ball is slowly vented unreacted oxygen.Reaction solution filtering, filtrate decompression revolving removal solvent, then pass through column chromatographic isolation and purification,
Obtain compound 6- phenyl -2- phenylimidazole [1,2-a] pyridine -3- aldehyde, the step yield 75%.
Embodiment 5
0.2 mM of pyridine of addition compound 6- trifluoromethyl -2- phenylimidazole [1,2-a] in the test tube of 25mL, three
0.1 mM of nitric hydrate copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on filled with oxygen
Balloon stirs under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes gas
Ball is slowly vented unreacted oxygen.Reaction solution filtering, filtrate decompression revolving removal solvent, then pass through column chromatographic isolation and purification,
Obtain compound 6- trifluoromethyl -2- phenylimidazole [1,2-a] pyridine -3- aldehyde, the step yield 45%.
Embodiment 6
0.2 mM of pyridine of compound 2- (p-methylphenyl) imidazoles [1,2-a], three hydration nitre are added in the test tube of 25mL
0.1 mM of sour copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the balloon filled with oxygen,
It is stirred under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes balloon, is delayed
The empty unreacted oxygen of slow play.Reaction solution filtering, filtrate decompression revolving removal solvent, then by column chromatographic isolation and purification, obtain
Compound 2- (p-methylphenyl) imidazoles [1,2-a] pyridine -3- aldehyde, the step yield 85%.
Embodiment 7
0.2 mM of pyridine of compound 2- (4- methoxyphenyl) imidazoles [1,2-a] is added in the test tube of 25mL, three water
0.1 mM of copper nitrate is closed, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the gas filled with oxygen
Ball stirs under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes gas
Ball is slowly vented unreacted oxygen.Reaction solution filtering, filtrate decompression revolving removal solvent, then pass through column chromatographic isolation and purification,
Obtain compound 2- (4- methoxyphenyl) imidazoles [1,2-a] pyridine -3- aldehyde, the step yield 80%.
Embodiment 8
0.2 mM of pyridine of compound 2- (4- fluorophenyl) imidazoles [1,2-a], three hydration nitre are added in the test tube of 25mL
0.1 mM of sour copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the balloon filled with oxygen,
It is stirred under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes balloon, is delayed
The empty unreacted oxygen of slow play.Reaction solution filtering, filtrate decompression revolving removal solvent, then by column chromatographic isolation and purification, obtain
Compound 2- (4- fluorophenyl) imidazoles [1,2-a] pyridine -3- aldehyde, the step yield 70%.
Embodiment 9
0.2 mM of pyridine of compound 2- (4- chlorphenyl) imidazoles [1,2-a], three hydration nitre are added in the test tube of 25mL
0.1 mM of sour copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the balloon filled with oxygen,
It is stirred under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes balloon, is delayed
The empty unreacted oxygen of slow play.Reaction solution filtering, filtrate decompression revolving removal solvent, then by column chromatographic isolation and purification, obtain
Compound 2- (4- chlorphenyl) imidazoles [1,2-a] pyridine -3- aldehyde, the step yield 72%.
Embodiment 10
0.2 mM of pyridine of compound 2- (4- bromophenyl) imidazoles [1,2-a], three hydration nitre are added in the test tube of 25mL
0.1 mM of sour copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the balloon filled with oxygen,
It is stirred under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes balloon, is delayed
The empty unreacted oxygen of slow play.Reaction solution filtering, filtrate decompression revolving removal solvent, then by column chromatographic isolation and purification, obtain
Compound 2- (4- bromophenyl) imidazoles [1,2-a] pyridine -3- aldehyde, the step yield 65%.
Embodiment 11
0.2 mM of pyridine of compound 2- (4- phenyl) imidazoles [1,2-a], three hydrations are added in the test tube of 25mL
0.1 mM of copper nitrate, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on the gas filled with oxygen
Ball stirs under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes gas
Ball is slowly vented unreacted oxygen.Reaction solution filtering, filtrate decompression revolving removal solvent, then pass through column chromatographic isolation and purification,
Obtain compound 2- (4- phenyl) imidazoles [1,2-a] pyridine -3- aldehyde, the step yield 70%.
Embodiment 12
0.2 mM of pyridine of addition compound 2- (4- trifluoromethyl) imidazoles [1,2-a] in the test tube of 25mL, three
0.1 mM of nitric hydrate copper, 2 milliliters of addition n,N-Dimethylformamide (DMF) are used as reaction dissolvent, put on filled with oxygen
Balloon stirs under 130 degrees Celsius.Reaction solution is cooled to room temperature after reaction by TLC (thin-layered chromatography) detection, removes gas
Ball is slowly vented unreacted oxygen.Reaction solution filtering, filtrate decompression revolving removal solvent, then pass through column chromatographic isolation and purification,
Obtain compound 2- (4- trifluoromethyl) imidazoles [1,2-a] pyridine -3- aldehyde, the step yield 50%.
Claims (5)
1. a kind of 2- phenylimidazole [1,2-a] replaced with DMF (N,N-dimethylformamide) for the building of one step of formylation reagent
The new method of pyridine -3- aldehyde, which is characterized in that synthetic route is as follows:
Specific steps are as follows:
It takes compound 1 to be placed in container, promotor and solvent is added, puts on the balloon filled with oxygen gas, is stirred to react 1-48
Hour, it is cooled to room temperature after reaction, removes balloon, reaction solution filters, and after evaporating solvent under reduced pressure, crude product is obtained, through column layer
2- phenylimidazole [1,2-a] pyridine -3- aldehyde that analysis purification is replaced.
Wherein, R1 includes methyl, F, Cl, phenyl, trifluoromethyl；R2 includes methyl, methoxyl group, F, Cl, Br, phenyl, fluoroform
Base.
2. a kind of constructed with DMF (N,N-dimethylformamide) for one step of formylation reagent according to claim 1 replaces
2- phenylimidazole [1,2-a] pyridine -3- aldehyde new method, which is characterized in that the compound 1 be replace 2- phenylimidazole
[1,2-a] pyridine, the promotor are Gerhardite, and the solvent is DMF (n,N-Dimethylformamide).
3. a kind of constructed with DMF (N,N-dimethylformamide) for one step of formylation reagent according to claim 1 replaces
2- phenylimidazole [1,2-a] pyridine -3- aldehyde new method, which is characterized in that the container of the specific steps be teat glass.
4. a kind of constructed with DMF (N,N-dimethylformamide) for one step of formylation reagent according to claim 1 replaces
2- phenylimidazole [1,2-a] pyridine -3- aldehyde new method, which is characterized in that in the specific steps be added mantoquita amount with
The molar ratio of compound 1 (substituted 2- phenylimidazole [1,2-a] pyridine) is 0.5:1.
5. a kind of constructed with DMF (N,N-dimethylformamide) for one step of formylation reagent according to claim 1 replaces
2- phenylimidazole [1,2-a] pyridine -3- aldehyde new method, which is characterized in that filled with oxygen gas described in the specific steps
The balloon pressure of body is 1 atmospheric pressure.
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| CN201910712813.6A CN110372694A (en) | 2019-08-02 | 2019-08-02 | A kind of new method of 2- phenylimidazole [1,2-a] pyridine -3- aldehyde replaced using DMF as formylation reagent building |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114292230A (en) * | 2022-02-27 | 2022-04-08 | 桂林理工大学 | Palladium-catalyzed N-phenylpyridine-2-amine N-H carbonylation reaction taking DMF as methyl source |
-
2019
- 2019-08-02 CN CN201910712813.6A patent/CN110372694A/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114292230A (en) * | 2022-02-27 | 2022-04-08 | 桂林理工大学 | Palladium-catalyzed N-phenylpyridine-2-amine N-H carbonylation reaction taking DMF as methyl source |
| CN114292230B (en) * | 2022-02-27 | 2023-11-17 | 桂林理工大学 | Palladium catalyzed N-H carbonylation of N-phenylpyridine-2-amine with DMF as methyl source |
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Application publication date: 20191025 |