CN104844598A - Synthesis method of 8-methoxy ethyl formate imidazole and [1,2a]pyridine-3-ethyl formate - Google Patents
Synthesis method of 8-methoxy ethyl formate imidazole and [1,2a]pyridine-3-ethyl formate Download PDFInfo
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- CN104844598A CN104844598A CN201510214949.6A CN201510214949A CN104844598A CN 104844598 A CN104844598 A CN 104844598A CN 201510214949 A CN201510214949 A CN 201510214949A CN 104844598 A CN104844598 A CN 104844598A
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- methoxy methyl
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- nicotinicum acidum
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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
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Abstract
The invention relates to a synthesis method of 8-methoxy ethyl formate imidazole and [1,2a]pyridine-3-ethyl formate. The synthesis method includes the following steps: enabling 2-amino-3-hydroxypyridine and DMF-DMA to react at a certain ratio at 25-105 DEG C to obtain an N,N-dimethyl-N'-(3-hydroxypyridine-2-base) formamidine intermediate; enabling the intermediate to react with ethyl bromoacetate of a certain proportion at 30-150 DEG C to generate 8-methoxy ethyl formate imidazole and [1,2a]pyridine-3-ethyl formate. The synthesis method is easy-to-get in reaction raw material, reasonable in price, mild in reaction condition, easy in operation and control and simple in aftertreatment, and the product is stable in quality and high in purity.
Description
(1) technical field
The invention belongs to organic synthesis field, be specifically related to a kind of synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester.
(2) background technology
Have submitted a kind of 3-aldehyde radical-6-bromine imidazo [1 on March 11st, 2015,2-a] synthetic method of pyridine-8-ethyl formate: 100mmol (16.6g) 2-aminonicotinate and 110mmol (19.58g) N-bromo-succinimide 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.The 2-amino-5-bromo-nicotinic acid ethyl ester (24.1g obtained, 98.36mmol) solid is placed in 250ml single port flask, add 200mL N, N-dimethylformamide dimethyl acetal, react 5 hours at 70 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 3-ethyl formate-5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, N-dimethylformamide dimethyl acetal, add the aqueous chloroacetaldehyde solution (25.09g of 40 percent, monochloroacetaldehyde 127.86mmol), 60 DEG C are 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 300ml 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 13.0g sterling.
8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester 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 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester.
The present invention is achieved through the following technical solutions:
A kind of synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, its special character is: comprise the following steps:
(1) 2-amino-3-pyridone and DMF-DMA are in certain proportion, in certain solvent, react under 25-110 degree Celsius, obtained N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate, and this intermediate does not need to purify;
(2) this intermediate and a certain proportion of ethyl bromoacetate are reacted at 30-150 DEG C and are generated 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling is obtained after recrystallization is purified.
The synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester of the present invention, described solvent is ethyl acetate, the trimethyl carbinol, N,N-dimethylacetamide, acetonitrile and Virahol, methyl alcohol, one or both in DMF.
The synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester of the present invention, said alkali is saleratus, salt of wormwood, sodium bicarbonate, sodium carbonate.
The synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester of the present invention, described recrystallization solvent is the mixture of ethyl acetate and normal hexane.
The synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester of the present invention, described the first step feed ratio is 2-amino-3-pyridone: DMF-DMA=1:0.5-4.3.
The synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester of the present invention, described second step feed ratio is 2-amino-3-pyridone: ethyl bromoacetate=1:0.8-5.1.
The synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester of the present invention, step (1) reaction times is 3-10 hour, and step (2) reaction times is 6-15 hour.
Its reaction formula is:
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
2-amino-3-pyridone (1.10g, 10mmol) is added, DMF-DMA(1.19g, 10mmol in 50mL single necked round bottom flask), acetonitrile 15ml.Mixture in reaction flask stirring reaction 4 hours at 50 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (2.51g wherein, 15mmol), sodium bicarbonate (1.68g, 20mmol), trimethyl carbinol 15ml, mixture was 110 DEG C of reactions 10 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 81.50%, purity 98.00% (GC).Nuclear magnetic resonance spectroscopy: 1H NMR (deuterated DMSO): 8.97 ppm (s, 1H), 8.25ppm (s, 1H), 6.92ppm (s, 1H), 6.71ppm (s, 1H), 4.98 ppm (d, 2H), 4.41ppm (d, 2H), 4.27ppm (d, 2H), 1.41ppm (t, 3H), 1.29ppm (t, 3H).
Embodiment 2
2-amino-3-pyridone (2.20g, 20mmol) is added, DMF-DMA(4.77g, 40mmol in 50mL single necked round bottom flask), methyl alcohol 15ml.Mixture in reaction flask stirring reaction 4 hours at 50 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (6.68g wherein, 40mmol), sodium bicarbonate (3.36g, 40mmol), trimethyl carbinol 35ml, mixture was 110 DEG C of reactions 10 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 78.0%, purity 98.25% (GC).
Embodiment 3
2-amino-3-pyridone (2.20g, 20mmol) is added, DMF-DMA(1.79g, 15mmol in 50mL single necked round bottom flask), acetonitrile 10ml.Mixture in reaction flask stirring reaction 3 hours at 80 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (6.68g wherein, 40mmol), sodium bicarbonate (3.36g, 40mmol), trimethyl carbinol 35ml, mixture was 110 DEG C of reactions 10 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 67.15%, purity 98.40% (GC).
Embodiment 4
2-amino-3-pyridone (6.61g, 60mmol) is added, DMF-DMA(21.45g, 180mmol in 250mL single necked round bottom flask), trimethyl carbinol 100ml.Mixture in reaction flask stirring reaction 4 hours at 50 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (20.04g wherein, 120mmol), sodium bicarbonate (6.72g, 80mmol), DMF 100ml, mixture was 110 DEG C of reactions 10 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 69.31%, purity 98.62% (GC).
Embodiment 5
2-amino-3-pyridone (6.61g, 60mmol) is added, DMF-DMA(21.45g, 180mmol in 250mL single necked round bottom flask), acetonitrile 150ml.Mixture in reaction flask stirring reaction 4 hours at 50 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (20.04g wherein, 120mmol), sodium bicarbonate (6.72g, 80mmol), DMF 100ml, mixture was 130 DEG C of reactions 8 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 85%, purity 99.00% (GC).
Embodiment 6
2-amino-3-pyridone (6.61g, 60mmol) is added, DMF-DMA(28.60g, 240mmol in 250mL single necked round bottom flask), trimethyl carbinol 120ml.Mixture in reaction flask stirring reaction 4 hours at 50 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (20.04g wherein, 120mmol), sodium bicarbonate (6.72g, 80mmol), DMF 100ml, mixture was 150 DEG C of reactions 7 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 87.00%, purity 98.42% (GC).
Embodiment 7
2-amino-3-pyridone (1.10g, 10mmol) is added, DMF-DMA(1.19g, 10mmol in 50mL single necked round bottom flask), Virahol 10ml.Mixture in reaction flask stirring reaction 4 hours at 50 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (2.51g wherein, 15mmol), sodium bicarbonate (1.68g, 20mmol), trimethyl carbinol 15ml, mixture was 110 DEG C of reactions 10 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 82.39%, purity 98.40% (GC).
Embodiment 8
2-amino-3-pyridone (1.10g, 10mmol) is added, DMF-DMA(0.6g, 5mmol in 50mL single necked round bottom flask), ethyl acetate 10ml.Mixture in reaction flask stirring reaction 10 hours at 25 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (1.34g wherein, 8mol), sodium carbonate (2.12g, 20mmol), DMF15ml, mixture was 150 DEG C of reactions 6 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 82.44%, purity 98.40% (GC).
Embodiment 9
2-amino-3-pyridone (1.10g, 10mmol) is added, DMF-DMA(5.11g, 43mmol in 50mL single necked round bottom flask), N,N-dimethylacetamide 15ml.Mixture in reaction flask stirring reaction 3 hours at 110 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (8.54g wherein, 51mmol), saleratus (2g, 20mmol), methyl alcohol 15ml, mixture was 30 DEG C of reactions 15 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 82.47%, purity 98.22% (GC).
Embodiment 10
2-amino-3-pyridone (1.10g, 10mmol) is added, DMF-DMA(1.19g, 10mmol in 50mL single necked round bottom flask), DMF10ml.Mixture in reaction flask stirring reaction 4 hours at 100 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (2.51g wherein, 15mmol), salt of wormwood (2.76g, 20mmol), DMF15ml, mixture was 150 DEG C of reactions 10 hours, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 82.21%, purity 98.47% (GC).
Embodiment 11
2-amino-3-pyridone (1.10g, 10mmol) is added, DMF-DMA(5.11g, 43mmol in 50mL single necked round bottom flask), glycerine 25ml, ethanol 10ml.Mixture in reaction flask stirring reaction 0.3 hour at 170 DEG C.TLC and GC determines that reaction completes, and generates N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate.Rotary evaporation removes unnecessary solvent, add ethyl bromoacetate (8.54g wherein, 51mmol), saleratus (2g, 20mmol), glycerine 25ml, mixture was 170 DEG C of reactions 0.3 hour, and reaction terminates, and adds water and extraction into ethyl acetate, anhydrous sodium sulfate drying, revolve steaming, obtain 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, with obtaining 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling after ethyl acetate and hexane mixture recrystallization.Calculated yield 89.51%, purity 98.14% (GC).
Claims (7)
1. the synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1, a 2a] Nicotinicum Acidum ethyl ester, is characterized in that: comprise the following steps:
(1) 2-amino-3-pyridone and DMF-DMA are in certain proportion, in certain solvent, react under 25-110 degree Celsius, obtained N, N-dimethyl-N '-(3-pyridone-2-base) carbonamidine intermediate, and this intermediate does not need to purify;
(2) this intermediate and a certain proportion of ethyl bromoacetate are reacted at 30-150 DEG C and are generated 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester, 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester sterling is obtained after recrystallization is purified.
2. the synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester according to claim 1, is characterized in that: described solvent is ethyl acetate, the trimethyl carbinol, N,N-dimethylacetamide, acetonitrile and Virahol, methyl alcohol, one or both in DMF.
3. the synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester according to claim 1 and 2, is characterized in that: said alkali is saleratus, salt of wormwood, sodium bicarbonate, sodium carbonate.
4. the synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester according to claim 1 and 2, is characterized in that: described recrystallization solvent is the mixture of ethyl acetate and normal hexane.
5. the synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester according to claim 1 and 2, is characterized in that: described the first step feed ratio is 2-amino-3-pyridone: DMF-DMA=1:0.5-4.3.
6. the synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester according to claim 1 and 2, is characterized in that: described second step feed ratio is 2-amino-3-pyridone: ethyl bromoacetate=1:0.8-5.1.
7. the synthetic method of 8-methoxy methyl acetoacetic ester imidazo [1,2a] Nicotinicum Acidum ethyl ester according to claim 1 and 2, it is characterized in that: step (1) reaction times is 3-10 hour, step (2) reaction times is 6-15 hour.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106632351A (en) * | 2016-11-18 | 2017-05-10 | 山东友帮生化科技有限公司 | Method for preparing 6-bromine imidazo [1,2-a]pyrazine-3-nonanoic acid-ethyl ester |
| CN106831782A (en) * | 2016-11-23 | 2017-06-13 | 山东友帮生化科技有限公司 | The synthetic method of 6 chlorine imidazos [1,2 b] formic acid of pyridazine 3 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103965190A (en) * | 2014-05-20 | 2014-08-06 | 定陶县友帮化工有限公司 | Synthesis method of imidazo[1,2-alpha]pyridyl-3-formic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103965190A (en) * | 2014-05-20 | 2014-08-06 | 定陶县友帮化工有限公司 | Synthesis method of imidazo[1,2-alpha]pyridyl-3-formic acid |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632351A (en) * | 2016-11-18 | 2017-05-10 | 山东友帮生化科技有限公司 | Method for preparing 6-bromine imidazo [1,2-a]pyrazine-3-nonanoic acid-ethyl ester |
| CN106831782A (en) * | 2016-11-23 | 2017-06-13 | 山东友帮生化科技有限公司 | The synthetic method of 6 chlorine imidazos [1,2 b] formic acid of pyridazine 3 |
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Application publication date: 20150819 |