CN104402882A - Synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate - Google Patents
Synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate Download PDFInfo
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- CN104402882A CN104402882A CN201410615287.9A CN201410615287A CN104402882A CN 104402882 A CN104402882 A CN 104402882A CN 201410615287 A CN201410615287 A CN 201410615287A CN 104402882 A CN104402882 A CN 104402882A
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- pyridine
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- 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
- C07D471/04—Ortho-condensed systems
Abstract
The invention relates to a synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate. The method comprises the following steps: carrying out a substitution reaction on ethyl 2-aminonicotinate and N-chlorosuccinimide in a certain solvent at normal temperature to prepare ethyl 2-amino-5-chloronicotinate; and reacting2-amino-5-chloronicotinate with N,N-dimethylformamide dimethyl acetal to prepare an intermediate, reacting the intermediate with chloroacetaldehyde in a certain solvent at 0-100DEG C without purifying the intermediate, cooling, and drying to obtain ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate. The method has the advantages of easily available reaction raw materials, reasonable price, mild reaction conditions, easy operation, easy control and simple post-treatment, and the above obtained product has the advantages of stable quality and high purity.
Description
(1) technical field
The invention belongs to organic synthesis field, be specifically related to a kind of synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate.
(2) background technology
3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate is the important intermediate of organic synthesis, is mainly used in medicine intermediate, organic synthesis, organic solvent, also can be applicable to the aspects such as DYE PRODUCTION, pesticide producing and spices.This product is novel medicine intermediate, and have very large medical value, it synthesizes difficulty, and market value is expensive, lacks document and Patents report.
(3) summary of the invention
The present invention needs the problem solved to be for prior art, and provide a kind of technique advantages of simple, cost low, product purity is high, is suitable for the synthetic method of industrialized 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate.
The present invention is achieved through the following technical solutions:
A kind of synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate, its special character is: comprise the following steps:
(1) 2-aminonicotinate elder generation is with N-chlorosuccinimide under certain solvent, under normal temperature, substitution reaction occurs, obtained 2-amino-5-chlorine apellagrin ethyl ester;
(2) 2-amino-5-chlorine apellagrin ethyl ester and N, dinethylformamide dimethylacetal reacts to obtain intermediate, this intermediate does not need to purify, in certain solvent, react at 0-100 DEG C with monochloroacetaldehyde, reaction terminates, cooling, drying, obtains 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate.
3-aldehyde radical-6-chlorine imidazo [1 of the present invention, 2-a] synthetic method of pyridine-8-ethyl formate, in step (2), intermediate and monochloroacetaldehyde react and terminate, be cooled to room temperature, add appropriate alkali, leave standstill and separate out solid, solid is dissolved in ethyl acetate, obtains 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate with water and the washing of saturated aqueous common salt priority, anhydrous sodium sulfate drying, rotary evaporation after concentrating.
The synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate of the present invention, intermediate and monochloroacetaldehyde react 3-15 hour.
The synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate of the present invention, in step (1), solvent is acetonitrile, DMF.
The synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate of the present invention, in step (2), DMF dimethylacetal is reactant is also solvent.
The synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate of the present invention, in step (2), solvent is water, DMF.
The synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate of the present invention, described alkali is sodium hydroxide, sodium bicarbonate, sodium carbonate.
3-aldehyde radical-6-chlorine imidazo [1 of the present invention, 2-a] synthetic method of pyridine-8-ethyl formate, 2-amino-5-chlorine apellagrin ethyl ester and N, the temperature of reaction of dinethylformamide dimethylacetal is 60 DEG C, 80 DEG C, 100 DEG C, and the temperature of reaction of intermediate and monochloroacetaldehyde is 0 DEG C, 60 DEG C and 100 DEG C.
Synthesis technique and the synthesis step of 6-chlorine imidazo [1,2-a] Nicotinicum Acidum of the present invention are as follows:
Beneficial effect of the present invention: reaction raw materials compares and is easy to get, reasonable price, reaction conditions is gentle, easy handling, is easy to control, and aftertreatment is simple, and constant product quality, purity is high.
(4) embodiment
Embodiment 1
100mmol (16.6g) 2-aminonicotinate and 110mmol (14.69g) N-chlorosuccinimide react in 200ml acetonitrile, normal-temperature reaction three hours.Be placed on after reaction terminates in the environment of zero degrees celsius and leave standstill three hours, suction filtration, filter cake acetonitrile drip washing, obtains 24.1g solid, productive rate 98.36%.Acetonitrile revolves to steam and reclaims.
Get 2-amino-5-chlorine apellagrin ethyl ester (10g, 50mmol) solid is placed in 250ml single port flask, add 100mL N, dinethylformamide dimethylacetal, react 5 hours at 60 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the chloro-pyridine of 3-ethyl formate-5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add the aqueous chloroacetaldehyde solution (12.76g of 40 percent, monochloroacetaldehyde 65mmol), 0 DEG C is reacted 10 hours, reaction terminates, be chilled to room temperature, add appropriate saturated sodium bicarbonate solution, PH is regulated to approximate 8.Leave standstill three hours, separate out solid, all solids is dissolved in 200ml ethyl acetate, wash three times with water, each 100ml, object removes unnecessary monochloroacetaldehyde, then uses saturated common salt water washing 2 times, each 100ml, then concentrated with anhydrous sodium sulfate drying, rotary evaporation, dry after 4.0g sterling.Productive rate 34.4%.1HNMR(400MHz，DMSO)δ:10.339(s,1H),9.351(s,1H),8.593(s, 1H),8.318(s, 1H), 4.364(q,J=8.0Hz,2H), 1.344(t,J=8.0Hz,3H) 。
Embodiment 2
100mmol (16.6g) 2-aminonicotinate and 110mmol (14.69g) N-chlorosuccinimide react in 200ml acetonitrile, normal-temperature reaction three hours.Be placed on after reaction terminates in the environment of zero degrees celsius and leave standstill three hours, suction filtration, filter cake acetonitrile drip washing, obtains 24.0g solid, productive rate 97.9%.Acetonitrile revolves to steam and reclaims.
Get 2-amino-5-chlorine apellagrin ethyl ester (10g, 50mmol) solid is placed in 250ml single port flask, add 100mL N, dinethylformamide dimethylacetal, react 5 hours at 100 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the chloro-pyridine of 3-ethyl formate-5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add the aqueous chloroacetaldehyde solution (14.72g of 40 percent, monochloroacetaldehyde 75mmol), 60 DEG C are reacted 15 hours, reaction terminates, be chilled to room temperature, add appropriate sodium hydroxide solution, PH is regulated to approximate 8.Leave standstill three hours, separate out solid, solid is dissolved in 200ml ethyl acetate, wash three times with water, each 100ml, object removes unnecessary monochloroacetaldehyde, then uses saturated common salt water washing 2 times, each 100ml, then concentrated with anhydrous sodium sulfate drying, rotary evaporation, dry after must obtain 8.2g sterling.Productive rate 70.68%.1HNMR(400MHz，DMSO)δ:10.339(s,1H),9.351(s,1H),8.593(s, 1H),8.318(s, 1H), 4.364(q,J=8.0Hz,2H), 1.344(t,J=8.0Hz,3H) 。
Embodiment 3
100mmol (16.6g) 2-aminonicotinate and 110mmol (14.69g) N-chlorosuccinimide react in 200ml acetonitrile, normal-temperature reaction three hours.Be placed on after reaction terminates in the environment of zero degrees celsius and leave standstill three hours, suction filtration obtains 22.9g solid.Productive rate 93.46%.
Get (10g, 50mmol) solid of 2-amino-5-chlorine apellagrin ethyl ester is placed in 250ml single port flask, add 100mL N, dinethylformamide dimethylacetal, with 80 DEG C at react 8 hours, reaction terminates obtained N, N-dimethyl-N'-2-(the chloro-pyridine of 3-ethyl formate-5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add aqueous chloroacetaldehyde solution (13.74g, monochloroacetaldehyde 70mmol) and the 20ml water of 40 percent.100 DEG C are reacted 3 hours, and reaction terminates, and is chilled to room temperature, adds appropriate saturated sodium carbonate solution, regulate PH to approximate 8.Leave standstill three hours, separate out solid, solid is dissolved in 200ml ethyl acetate, wash three times with water, each 100ml, object removes unnecessary monochloroacetaldehyde, then uses saturated common salt water washing 2 times, each 100ml, then concentrated with anhydrous sodium sulfate drying, rotary evaporation, dry after 6.1g sterling.Productive rate 52.58%1HNMR (400MHz, DMSO) δ: 10.339 (s, 1H), 9.351 (s, 1H), 8.593 (s, 1H), 8.318 (s, 1H), 4.364 (q, J=8.0Hz, 2H), 1.344 (t, J=8.0Hz, 3H).
Embodiment 4
100mmol (16.6g) 2-aminonicotinate and 110mmol (14.69g) N-chlorosuccinimide react in 200ml acetonitrile, normal-temperature reaction three hours.Be placed on after reaction terminates in the environment of zero degrees celsius and leave standstill three hours, suction filtration obtains 22.9g solid.Productive rate 93.46%.
Get (10g, 50mmol) solid of 2-amino-5-chlorine apellagrin ethyl ester is placed in 250ml single port flask, add 100mL N, dinethylformamide dimethylacetal, with 100 DEG C at react 8 hours, reaction terminates obtained N, N-dimethyl-N'-2-(the chloro-pyridine of 3-ethyl formate-5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add aqueous chloroacetaldehyde solution (14.72g, monochloroacetaldehyde 75mmol) and the 50ml water of 40 percent.60 DEG C are reacted 15 hours, and reaction terminates, and is chilled to room temperature, adds appropriate saturated sodium carbonate solution, regulate PH to approximate 8.Leave standstill three hours, separate out solid, solid is dissolved in 200ml ethyl acetate, wash three times with water, use 100ml at every turn, object removes unnecessary monochloroacetaldehyde, then saturated common salt water washing is used 2 times, each 100ml, then concentrated with anhydrous sodium sulfate drying, rotary evaporation, dry after, obtain 5.3g sterling.Productive rate 45.68%1HNMR (400MHz, DMSO) δ: 10.339 (s, 1H), 9.351 (s, 1H), 8.593 (s, 1H), 8.318 (s, 1H), 4.364 (q, J=8.0Hz, 2H), 1.344 (t, J=8.0Hz, 3H).
Embodiment 5
100mmol (16.6g) 2-aminonicotinate and 110mmol (14.69g) N-chlorosuccinimide, at 200mlN, react in dinethylformamide, normal-temperature reaction three hours.Be placed on after reaction terminates in the environment of zero degrees celsius and leave standstill three hours, suction filtration obtains 22.9g solid.Productive rate 93.46%.
Get (10g, 50mmol) solid of 2-amino-5-chlorine apellagrin ethyl ester is placed in 250ml single port flask, add 100mL N, dinethylformamide dimethylacetal, with 70 DEG C at react 10 hours, reaction terminates obtained N, N-dimethyl-N'-2-(the chloro-pyridine of 3-ethyl formate-5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add aqueous chloroacetaldehyde solution (14.72g, monochloroacetaldehyde 75mmol) and the 50ml DMF of 40 percent.60 DEG C are reacted 15 hours, and reaction terminates, and is chilled to room temperature, adds appropriate saturated sodium carbonate solution, regulate PH to approximate 8.Leave standstill three hours, separate out solid, solid is dissolved in 200ml ethyl acetate, wash three times with water, each 100ml, object removes unnecessary monochloroacetaldehyde, then uses saturated common salt water washing 2 times, each 100ml, then concentrated with anhydrous sodium sulfate drying, rotary evaporation, dry after must obtain 5.6g sterling.Productive rate 48.26%1HNMR (400MHz, DMSO) δ: 10.339 (s, 1H), 9.351 (s, 1H), 8.593 (s, 1H), 8.318 (s, 1H), 4.364 (q, J=8.0Hz, 2H), 1.344 (t, J=8.0Hz, 3H).
Embodiment 6
100mmol (16.6g) 2-aminonicotinate and 110mmol (14.69g) N-chlorosuccinimide, at 200mlN, react in dinethylformamide, normal-temperature reaction three hours.Be placed on after reaction terminates in the environment of zero degrees celsius and leave standstill three hours, suction filtration obtains 22.9g solid.Productive rate 93.46%.
Get (10g, 50mmol) solid of 2-amino-5-chlorine apellagrin ethyl ester is placed in 250ml single port flask, add 100mL N, dinethylformamide dimethylacetal, with 90 DEG C at react 7 hours, reaction terminates obtained N, N-dimethyl-N'-2-(the chloro-pyridine of 3-ethyl formate-5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add aqueous chloroacetaldehyde solution (14.72g, monochloroacetaldehyde 75mmol) and the 50ml DMF of 40 percent.40 DEG C are reacted 10 hours, and reaction terminates, and is chilled to room temperature, adds appropriate saturated sodium carbonate solution, regulate PH to approximate 8.Leave standstill three hours, separating out solid solid is dissolved in 200ml ethyl acetate, wash three times with water, each 100ml, object removes unnecessary monochloroacetaldehyde, then uses saturated common salt water washing 2 times, each 100ml, then concentrated with anhydrous sodium sulfate drying, rotary evaporation, dry after, obtain 5.5g sterling.Productive rate 47.4%1HNMR (400MHz, DMSO) δ: 10.339 (s, 1H), 9.351 (s, 1H), 8.593 (s, 1H), 8.318 (s, 1H), 4.364 (q, J=8.0Hz, 2H), 1.344 (t, J=8.0Hz, 3H).
Claims (8)
1. the synthetic method of 3-aldehyde radical-6-chlorine imidazo [1, a 2-a] pyridine-8-ethyl formate, is characterized in that: comprise the following steps:
(1) 2-aminonicotinate elder generation is with N-chlorosuccinimide under certain solvent, under normal temperature, substitution reaction occurs, obtained 2-amino-5-chlorine apellagrin ethyl ester;
(2) 2-amino-5-chlorine apellagrin ethyl ester and N, dinethylformamide dimethylacetal reacts to obtain intermediate, this intermediate does not need to purify, in certain solvent, react at 0-100 DEG C with monochloroacetaldehyde, reaction terminates, cooling, drying, obtains 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate.
2. 3-aldehyde radical-6-chlorine imidazo [1 according to claim 1,2-a] synthetic method of pyridine-8-ethyl formate, it is characterized in that: in step (2), intermediate and monochloroacetaldehyde react and terminate, be cooled to room temperature, add appropriate alkali, leave standstill and separate out solid, solid is dissolved in ethyl acetate, obtains 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate with water and the washing of saturated aqueous common salt priority, anhydrous sodium sulfate drying, rotary evaporation after concentrating.
3. the synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate according to claim 1 and 2, is characterized in that: intermediate and monochloroacetaldehyde react 3-15 hour.
4. the synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate according to claim 1 and 2, it is characterized in that: in step (1), solvent is acetonitrile, DMF.
5. the synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate according to claim 1 and 2, it is characterized in that: in step (2), DMF dimethylacetal is reactant is also solvent.
6. the synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate according to claim 1 and 2, it is characterized in that: in step (2), solvent is water, DMF.
7. the synthetic method of 3-aldehyde radical-6-chlorine imidazo [1,2-a] pyridine-8-ethyl formate according to claim 1 and 2, is characterized in that: described alkali is sodium hydroxide, sodium bicarbonate, sodium carbonate.
8. 3-aldehyde radical-6-chlorine imidazo [1 according to claim 1 and 2,2-a] synthetic method of pyridine-8-ethyl formate, it is characterized in that: 2-amino-5-chlorine apellagrin ethyl ester and N, the temperature of reaction of dinethylformamide dimethylacetal is 60 DEG C, 80 DEG C, 100 DEG C, and the temperature of reaction of intermediate and monochloroacetaldehyde is 0 DEG C, 60 DEG C and 100 DEG C.
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Cited By (3)
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| CN104876926A (en) * | 2015-03-31 | 2015-09-02 | 山东友帮生化科技有限公司 | Synthetic method for imidazo-[1, 2a]-3,8-PET |
| CN104876925A (en) * | 2015-03-31 | 2015-09-02 | 山东友帮生化科技有限公司 | Synthesis method for 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate |
| CN112225736A (en) * | 2020-11-12 | 2021-01-15 | 山东省科学院菏泽分院 | Preparation method of 6-bromoimidazo [1.2-a ] pyridine-3-formaldehyde |
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Cited By (3)
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| CN104876926A (en) * | 2015-03-31 | 2015-09-02 | 山东友帮生化科技有限公司 | Synthetic method for imidazo-[1, 2a]-3,8-PET |
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| CN112225736A (en) * | 2020-11-12 | 2021-01-15 | 山东省科学院菏泽分院 | Preparation method of 6-bromoimidazo [1.2-a ] pyridine-3-formaldehyde |
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