CN104844596A - Synthesis method for 6-bromoimidazo[1, 2-a]pyridine-3-phenyl ketone - Google Patents
Synthesis method for 6-bromoimidazo[1, 2-a]pyridine-3-phenyl ketone Download PDFInfo
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Abstract
The invention relates to a synthesis method for 6-bromoimidazo[1, 2-a]pyridine-3-phenyl ketone. The method includes: reacting N, N-dimethylformamide dimethylacetal with 2-amino-5-chloropyridine at 40-100DEG C to prepare an N, N-dimethyl-N'-2-(5-chloro-pyridine)yl-formamidine intermediate; without purification, reacting the intermediate with alpha-bromoacetophenone at 60-160DEG C in certain solvent under the action of alkali, at the end of reaction, conducting cooling to room temperature so as to precipitate high purity 6-chloroimidazo[1, 2-a]pyridine 3-phenyl ketone crystals, conducting pumping filtration, collecting the filter cake, adding water into the mother liquid, carrying out extraction, washing, drying and concentration to obtain a crude product, and subjecting the crude product to recrystallization so as to obtain a pure product. The method provided by the invention has the advantages of easily available reaction raw materials, reasonable price, mild reaction conditions, easy operation, easy control and simple aftertreatment. Also, the product has 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 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone.
(2) background technology
Phenyl ketone derivative is a kind of important medicine intermediate, a kind of method preparing fluorine-containing substituted phenyl ketone that on June 20th, 2012 announces, and concrete preparation process is as follows:
(1) in 2000L reactor, tetrahydrofuran (THF) 712kg (5vol) is added, magnesium powder 28kg (1.4eq), drip containing main raw material 3, tetrahydrofuran (THF) (2vol) the solution 445kg of 5-difluoro bromobenzene 160kg, be prepared into Grignard reagent 3,5-difluorophenyl magnesium bromide;
(2) in another 3000L reactor, tetrahydrofuran (THF) 427kg (3vol) is added successively, cuprous chloride 5.7kg (0.07eq), aluminum chloride 7.7kg (0.07eq), acetic anhydride 169.3kg (2.0eq), temperature control 10 ± 2 DEG C drips above-mentioned Grignard reagent 3,5-difluorophenyl magnesium bromide, drips and finishes in this thermotonus 4h;
(3) reaction is finished, extraction, and the water washing of organic phase salt concentrates to obtain product 3,5-difluoro acetophenone 106kg, yield 82.0%, gas chromatographic purity (GC) 99.8%.
The nuclear magnetic data of 3,5-difluoro acetophenone is as follows: 1H-NMR (500MHZ, CDCl
3), δ 2.55 (-CH
3on H), δ 7.34 (H on phenyl ring 2 and 6), δ 6.87 (H on phenyl ring 4).
Aforesaid method cheaper starting materials is easy to get, and reaction purity and yield is all higher, and stable process conditions is simple to operate, is applicable to large-scale production.
6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone 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 heterogeneous ring compound is new synthesis, and product is novel, has very large value.
(3) summary of the invention
The present invention needs the problem solved to be for prior art, the invention provides a kind of synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone, and this brand-new compound has very large Application in Chemical Engineering and is worth.Technique is simple, and meet the chemical concept of environmental protection, this synthetic method is simple to operate, productive rate is high, is applicable to laboratory and suitability for industrialized production.
The present invention is achieved through the following technical solutions:
A kind of synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone, its special character is: comprise the following steps:
(1) N is prepared, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate: N, dinethylformamide dimethylacetal and 2-amino-5-bromopyridine react obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate at 40-100 DEG C;
(2) 6-bromine imidazo [1 is prepared, 2-a] pyridine-3-phenyl ketone: above-mentioned intermediate does not need to purify, under alkali effect, in certain solvent, react at 60-160 DEG C with alpha-brominated methyl phenyl ketone, reaction terminates, be chilled to room temperature, there is highly purified 6-bromine imidazo [1, 2-a] precipitation of pyridine 3-phenyl ketone crystal, suction filtration, collect filter cake, mother liquor adds water, extraction into ethyl acetate, water and saturated common salt water washing, anhydrous sodium sulfate drying, 6-bromine imidazo [1 is obtained after rotary evaporation is concentrated, 2-a] the thick product of pyridine 3-phenyl ketone, this thick product recrystallization obtains sterling.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, temperature described in step (1) is 40 DEG C, 60 DEG C, 80 DEG C, 100 DEG C.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, reaction times 2-8 hour described in step (2).
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, the reaction times described in step (1) is 3 hours, 6 hours, 8 hours.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, described in step (2), solvent is dioxane, toluene, DMF, at least one in N,N-dimethylacetamide.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, described in step (2), alkali is saleratus, salt of wormwood, sodium bicarbonate, sodium carbonate, sodium hydroxide, at least one in potassium hydroxide.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, temperature described in step (2) is 60 DEG C, 100 DEG C, 120 DEG C, 160 DEG C.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, the reaction times described in step (2) is 3-15 hour.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, the reaction times described in step (2) is 8 hours, 10 hours, 12 hours, 15 hours.
The synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone of the present invention, with the normal hexane of volume ratio 3:1 and ethyl acetate mixture recrystallization in step (2).
Its reaction 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
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, reacts 3 hours with at 2-amino-5-bromopyridine (34.6g, 200mmol) 40 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary DMF dimethylacetal, add 120 ml(125g) dioxane, NaHCO
3(25.2g, 300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 100 DEG C are reacted 10 hours, and reaction terminates, and is chilled to room temperature, is placed on refrigeration chamber 3 hours, suction filtration, obtain 32g6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 23g, altogether 55g product, productive rate 91.36%, fusing point: 142.8-146.4 DEG C, 1HNMR (400MHz, DMSO) δ: 9.708 (s, 1H), 8.248 (s, 1H), 7.862-7.79 (m, 4H), 7.668 (t, J=7.2Hz, 1H), 7.571 (t, J=7.6Hz, 2H).
Embodiment 2
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, reacts 6 hours with at 2-amino-5-bromopyridine (34.6g, 200mmol) 80 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary DMF dimethylacetal, add 120 ml(125g) dioxane, NaHCO
3(25.2g, 300mmol) and alpha-brominated methyl phenyl ketone (47.76g, 240mmol), 120 DEG C are reacted 8 hours, reaction terminates, and is chilled to room temperature, is placed on refrigeration chamber 3 hours, suction filtration, obtains 29g highly purified 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 20.5g, altogether 49.5g product, productive rate 82.2%, fusing point: 142.8-146.4 DEG C, 1HNMR (400MHz, DMSO) δ: 9.708 (s, 1H), 8.248 (s, 1H), 7.862-7.79 (m, 4H), 7.668 (t, J=7.2Hz, 1H), 7.571 (t, J=7.6Hz, 2H).
Embodiment 3
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with 2-amino-5-bromopyridine (34.6g, 200mmol) reaction 3 hours at 100 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 120 ml(125g) DMF, sodium hydroxide (12g, 300mmol) with alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 160 DEG C are reacted 8 hours, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 28g high purity 6-bromine imidazo [1, 2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 19.3g, altogether 47.3g product, productive rate 78.57%, fusing point: 142.8-146.4 DEG C, 1HNMR (400MHz, DMSO) δ: 9.708 (s, 1H), 8.248 (s, 1H), 7.862-7.79 (m, 4H), 7.668 (t, J=7.2Hz, 1H), 7.571 (t, J=7.6Hz, 2H).
Embodiment 4
67ml(60.08g, 500mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with 2-amino-5-bromopyridine (34.6g, 200mmol) reaction 8 hours at 100 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 120 ml(125g) dioxane, potassium hydroxide (16.8g, 300mmol) with alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 100 DEG C are reacted 12 hours, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 28.8g high purity 6-bromine imidazo [1, 2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 21.3g, altogether 50.1g product, productive rate 83.22%, fusing point: 142.8-146.4 DEG C, 1HNMR (400MHz, DMSO) δ: 9.708 (s, 1H), 8.248 (s, 1H), 7.862-7.79 (m, 4H), 7.668 (t, J=7.2Hz, 1H), 7.571 (t, J=7.6Hz, 2H).
Embodiment 5
67ml(60.08g, 500mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with 2-amino-5-bromopyridine (34.6g, 200mmol) reaction 8 hours at 60 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 120 ml toluene, saleratus (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 60 DEG C are reacted 15 hours, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 28.6g high purity 6-bromine imidazo [1, 2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 21.0g, altogether 49.6g product, fusing point: 142.7-146.2 DEG C.
Embodiment 6
67ml(60.08g, 500mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with 2-amino-5-bromopyridine (34.6g, 200mmol) reaction 8 hours at 90 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 120 mlN, N-N,N-DIMETHYLACETAMIDE, salt of wormwood (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 100 DEG C are reacted 11 hours, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 28.6g high purity 6-bromine imidazo [1, 2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 20.9g, altogether 49.5g product, fusing point: 142.7-146.2 DEG C.
Embodiment 7
67ml(60.08g, 500mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with 2-amino-5-bromopyridine (34.6g, 200mmol) reaction 7 hours at 90 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 120 mlN, N-N,N-DIMETHYLACETAMIDE, sodium carbonate (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 100 DEG C are reacted 8 hours, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 28.4g high purity 6-bromine imidazo [1, 2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 20.7g, altogether 49.1g product, fusing point: 142.7-146.2 DEG C.
Embodiment 8
310mmolN, dinethylformamide dimethylacetal is solvent and reaction raw materials, with 2-amino-5-bromopyridine (34.6g, 200mmol) reaction 0.5 hour at 102 DEG C, then 7ml dioxane is added, sodium carbonate (0.5g) and alpha-brominated methyl phenyl ketone (5g) react 0.4 hour, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 220 ml dioxane, sodium carbonate (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 102 DEG C are reacted 1 hour, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 28.8g high purity 6-bromine imidazo [1, 2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 21.5g, altogether 50.3g product, fusing point: 142.7-146.2 DEG C.
Embodiment 9
310mmolN, dinethylformamide dimethylacetal is solvent and reaction raw materials, with 2-amino-5-bromopyridine (34.6g, 200mmol) reaction 0.5 hour at 102 DEG C, then 7ml toluene is added, sodium carbonate (0.5g) and alpha-brominated methyl phenyl ketone (5g) 105 DEG C react 0.4 hour, reaction terminates obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 220 ml toluene, sodium carbonate (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 111 DEG C are reacted 1 hour, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 28.8g high purity 6-bromine imidazo [1, 2-a] pyridine-3-phenyl ketone crystal.Mother liquor adds 600 ml water and 200 ml extraction into ethyl acetate, separates organic phase, and aqueous phase is extracted with ethyl acetate (3 × 200 ml), merges organic phase, washes with water (2 × 150 ml), 200 ml saturated common salt water washings, anhydrous Na
2sO
4drying, filters, and obtains 6-bromine imidazo [1 after filtrate is concentrated, 2-a] the thick product of pyridine-3-phenyl ketone, this thick product is through normal hexane: ethyl acetate=3:1(volume ratio) mixing solutions recrystallization obtain sterling 21.8g, altogether 50.6g product, fusing point: 142.7-146.2 DEG C.
Claims (10)
1. the synthetic method of 6-bromine imidazo [1, a 2-a] pyridine-3-phenyl ketone, is characterized in that: comprise the following steps:
(1) N is prepared, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate: N, dinethylformamide dimethylacetal and 2-amino-5-bromopyridine react obtained N, N-dimethyl-N'-2-(the bromo-pyridine of 5-) base-carbonamidine intermediate at 40-100 DEG C;
(2) 6-bromine imidazo [1 is prepared, 2-a] pyridine-3-phenyl ketone: above-mentioned intermediate does not need to purify, under alkali effect, in certain solvent, react at 60-160 DEG C with alpha-brominated methyl phenyl ketone, reaction terminates, be chilled to room temperature, there is highly purified 6-bromine imidazo [1, 2-a] precipitation of pyridine 3-phenyl ketone crystal, suction filtration, collect filter cake, mother liquor adds water, extraction into ethyl acetate, water and saturated common salt water washing, anhydrous sodium sulfate drying, 6-bromine imidazo [1 is obtained after rotary evaporation is concentrated, 2-a] the thick product of pyridine 3-phenyl ketone, this thick product recrystallization obtains sterling.
2. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 1, is characterized in that: temperature described in step (1) is 40 DEG C, 60 DEG C, 80 DEG C, 100 DEG C.
3. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 1 and 2, is characterized in that: reaction times 2-8 hour described in step (2).
4. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 3, is characterized in that: the reaction times described in step (1) is 3 hours, 6 hours, 8 hours.
5. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 1 and 2, is characterized in that: described in step (2), solvent is dioxane, toluene, DMF, at least one in N,N-dimethylacetamide.
6. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 1 and 2, is characterized in that: described in step (2), alkali is saleratus, salt of wormwood, sodium bicarbonate, sodium carbonate, sodium hydroxide, at least one in potassium hydroxide.
7. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 1 and 2, is characterized in that: temperature described in step (2) is 60 DEG C, 100 DEG C, 120 DEG C, 160 DEG C.
8. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 1 and 2, is characterized in that: the reaction times described in step (2) is 3-15 hour.
9. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 8, is characterized in that: the reaction times described in step (2) is 8 hours, 10 hours, 12 hours, 15 hours.
10. the synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-phenyl ketone according to claim 1 and 2, is characterized in that: with the normal hexane of volume ratio 3:1 and ethyl acetate mixture recrystallization in step (2).
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US11939294B1 (en) | 2023-10-23 | 2024-03-26 | King Faisal University | 1-(2-(substituted phenyl)-2-oxoethyl)-3,5-dimethylpyridin-1-ium bromides as antitubercular agents |
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CN103965191A (en) * | 2014-05-20 | 2014-08-06 | 定陶县友帮化工有限公司 | Synthesis method of 6-bromoimidazo[1,2-alpha]pyridyl-3-formic acid |
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HUA CAO ETAL: "Transition Metal-Mediated C=O and C=C Bond-Forming Reactions:A Regioselective Strategy for the Synthesis of Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrazines", 《THE JOURNAL OF ORGANIC CHEMISTRY》 * |
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US11939294B1 (en) | 2023-10-23 | 2024-03-26 | King Faisal University | 1-(2-(substituted phenyl)-2-oxoethyl)-3,5-dimethylpyridin-1-ium bromides as antitubercular agents |
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