CN104876925A - Synthesis method for 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate - Google Patents

Synthesis method for 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate Download PDF

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CN104876925A
CN104876925A CN201510146395.0A CN201510146395A CN104876925A CN 104876925 A CN104876925 A CN 104876925A CN 201510146395 A CN201510146395 A CN 201510146395A CN 104876925 A CN104876925 A CN 104876925A
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pyridine
imidazo
ethyl formate
aldehyde radical
synthetic method
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崔淑芬
韩猛
来新胜
曹惊涛
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Shandong You Bang Biochemical Technology Co Ltd
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Shandong You Bang Biochemical Technology Co Ltd
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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
    • C07D471/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The present invention belongs to the field of organic synthesis, and particularly relates to a synthesis method for 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate, which comprises the following steps of obtaining a purification-free intermediate through the dimethyl acetal reaction between 2-amino-nicotinic acid ethyl ester and N, N-dimethyl formamide; reacting the intermediate with chloroacetaldehyde at 0-100 DEG C in a certain solvent, cooling the solvent after the reaction, adding alkali of a certain amount in the solvent to precipitate solids, and finally obtain 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate after the dissolving, drying and rotary evaporation process. The raw materials of the method are readily available, reasonable in cost, mild in reaction conditio, easy to operate and control, and simple in post-processing. Products obtained through the method are stable in quality and high in purity.

Description

A kind of synthetic method of 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate
(1) technical field
The invention belongs to organic synthesis field, be specifically related to a kind of synthetic method of 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate.
(2) background technology
3-aldehyde radical 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 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 imidazo [1,2-a] pyridine-8-ethyl formate, its special character is: comprise the following steps:
(1) 2-aminonicotinate and DMF dimethylacetal react to obtain intermediate, and this intermediate does not need to purify.
(2) intermediate is in certain solvent, reacts at 0-100 DEG C with monochloroacetaldehyde, and reaction terminates, and cooling, adds suitable alkali, separates out solid, dissolves, dry, revolves steaming, obtains 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate.
3-aldehyde radical 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 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 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 imidazo [1,2-a] pyridine-8-ethyl formate of the present invention, in step (1), DMF dimethylacetal is reactant is also solvent.
The synthetic method of 3-aldehyde radical 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 imidazo [1,2-a] pyridine-8-ethyl formate of the present invention, described alkali is sodium hydroxide, sodium bicarbonate, at least one in sodium carbonate.
3-aldehyde radical imidazo [1 of the present invention, 2-a] synthetic method of pyridine-8-ethyl formate, the temperature of reaction of 2-aminonicotinate and DMF 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 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate 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 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-(3-ethyl formate pyridine) 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 be about 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 12.0g sterling.Productive rate 55.04%.1HNMR(400MHz，DMSO)δ:10.38(d,J=9.6Hz, 1H), 9.50(d,J=9.6Hz, 1H), 8.51(dd,J=1.2Hz, J=4.8Hz, 1H), 8.31(dd, J=1.0Hz,J=7.6Hz, 1H),7.27(dd, JI=4.8Hz,J2=7.6Hz,1H),4.35(q,J=7.2Hz, 2H), 1.34(t, J=7.0Hz, 2H)。
Embodiment 2
100mmol (16.6g) 2-aminonicotinate 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-(3-ethyl formate pyridine) 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 be about 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 12.2g sterling.Productive rate 55.94%.1HNMR(400MHz，DMSO)δ:10.38(d,J=9.6Hz, 1H), 9.50(d,J=9.6Hz, 1H), 8.51(dd,J=1.2Hz, J=4.8Hz, 1H), 8.31(dd, J=1.0Hz,J=7.6Hz, 1H),7.27(dd, JI=4.8Hz,J2=7.6Hz,1H),4.35(q,J=7.2Hz, 2H), 1.34(t, J=7.0Hz, 2H)。
Embodiment 3
100mmol (16.6g) 2-aminonicotinate solid 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-(3-ethyl formate pyridine) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, adds 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 be about 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 11.1g sterling.Productive rate 50.91%.1HNMR(400MHz，DMSO)δ:10.38(d,J=9.6Hz, 1H), 9.50(d,J=9.6Hz, 1H), 8.51(dd,J=1.2Hz, J=4.8Hz, 1H), 8.31(dd, J=1.0Hz,J=7.6Hz, 1H),7.27(dd, JI=4.8Hz,J2=7.6Hz,1H),4.35(q,J=7.2Hz, 2H), 1.34(t, J=7.0Hz, 2H)。
Embodiment 4
100mmol (16.6g) 2-aminonicotinate solid 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-(3-ethyl formate pyridine) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, adds 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 12.3g sterling.Productive rate 56.4%1HNMR (400MHz, DMSO) δ: 10.38 (d, J=9.6Hz, 1H), 9.50 (d, J=9.6Hz, 1H), 8.51 (dd, J=1.2Hz, J=4.8Hz, 1H), 8.31 (dd, J=1.0Hz, J=7.6Hz, 1H), 7.27 (dd, JI=4.8Hz, J2=7.6Hz, 1H), 4.35 (q, J=7.2Hz, 2H), 1.34 (t, J=7.0Hz, 2H).
Embodiment 5
100mmol (16.6g) 2-aminonicotinate solid 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-(3-ethyl formate pyridine) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add the aqueous chloroacetaldehyde solution (14.72g of 40 percent, monochloroacetaldehyde 75mmol) and 50ml DMF.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 be about 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 10.6g sterling.Productive rate 48.62%1HNMR (400MHz, DMSO) δ: 10.38 (d, J=9.6Hz, 1H), 9.50 (d, J=9.6Hz, 1H), 8.51 (dd, J=1.2Hz, J=4.8Hz, 1H), 8.31 (dd, J=1.0Hz, J=7.6Hz, 1H), 7.27 (dd, JI=4.8Hz, J2=7.6Hz, 1H), 4.35 (q, J=7.2Hz, 2H), 1.34 (t, J=7.0Hz, 2H).
Embodiment 6
100mmol (16.6g) 2-aminonicotinate solid 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-(3-ethyl formate pyridine) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add the aqueous chloroacetaldehyde solution (14.72g of 40 percent, monochloroacetaldehyde 75mmol) and 50ml DMF.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 be about 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 9.5g sterling.Productive rate 43.7%1HNMR (400MHz, DMSO) δ: 10.38 (d, J=9.6Hz, 1H), 9.50 (d, J=9.6Hz, 1H), 8.51 (dd, J=1.2Hz, J=4.8Hz, 1H), 8.31 (dd, J=1.0Hz, J=7.6Hz, 1H), 7.27 (dd, JI=4.8Hz, J2=7.6Hz, 1H), 4.35 (q, J=7.2Hz, 2H), 1.34 (t, J=7.0Hz, 2H).
Embodiment 6
100mmol (16.6g) 2-aminonicotinate solid is placed in 250ml single port flask, add 100mL N, dinethylformamide dimethylacetal, then after reacting 5min at adding 60 DEG C, add the aqueous chloroacetaldehyde solution (1.472g of 40 percent, monochloroacetaldehyde 7.5mmol), reaction 5min, then 90 DEG C are warming up to, after reaction 25min, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add the aqueous chloroacetaldehyde solution (14.72g of 40 percent, monochloroacetaldehyde 75mmol), 4ml ethyl acetate, 85 DEG C of reaction 40min, reaction terminates, be chilled to room temperature, add appropriate sodium hydroxide solution, pH is regulated to be about 8.Leave standstill 1 hour, 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 use saturated common salt water washing 2 times, each 100ml, then concentrated with anhydrous sodium sulfate drying, rotary evaporation, dry after must obtain sterling.Productive rate 75.41%.

Claims (7)

1. the synthetic method of 3-aldehyde radical imidazo [1, a 2-a] pyridine-8-ethyl formate, is characterized in that: comprise the following steps:
(1) 2-aminonicotinate first reacts to obtain intermediate with DMF dimethylacetal, and this intermediate does not need to purify;
(2) intermediate is in certain solvent, reacts at 0-100 DEG C with monochloroacetaldehyde, and reaction terminates, and cooling is dry, obtains 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate.
2. 3-aldehyde radical 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, and are cooled to room temperature, add appropriate alkali, leave standstill and separate out solid, solid is dissolved in ethyl acetate, obtains 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate after concentrating with water and saturated aqueous common salt successively washing, anhydrous sodium sulfate drying, rotary evaporation.
3. the synthetic method of 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate according to claim 1 and 2, is characterized in that: in step (2), intermediate and monochloroacetaldehyde react 3-15 hour.
4. the synthetic method of 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate according to claim 1 and 2, is characterized in that: in step (2), solvent is water, 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 (1), DMF dimethylacetal is reactant is also solvent.
6. the synthetic method of 3-aldehyde radical imidazo [1,2-a] pyridine-8-ethyl formate according to claim 2, is characterized in that: described alkali is sodium hydroxide, sodium bicarbonate, at least one in sodium carbonate.
7. the 3-aldehyde radical imidazo [1 according to claim 2 or 5,2-a] synthetic method of pyridine-8-ethyl formate, it is characterized in that: 2-aminonicotinate 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, 100 DEG C.
CN201510146395.0A 2015-03-31 2015-03-31 Synthesis method for 3-aldehyde imidazo-[1, 2-alpha] pyridine-8-ethyl formate Pending CN104876925A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104402881A (en) * 2014-11-05 2015-03-11 定陶县友帮化工有限公司 Synthetic method of ethyl 3-aldehyde-6-bromoimidazo[1,2-a]pyridine-8-formate
CN104402882A (en) * 2014-11-05 2015-03-11 定陶县友帮化工有限公司 Synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104402881A (en) * 2014-11-05 2015-03-11 定陶县友帮化工有限公司 Synthetic method of ethyl 3-aldehyde-6-bromoimidazo[1,2-a]pyridine-8-formate
CN104402882A (en) * 2014-11-05 2015-03-11 定陶县友帮化工有限公司 Synthetic method of ethyl 3-aldehyde-6-chloroimidazo[1,2-a]pyridine-8-formate

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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Application publication date: 20150902