CN104844595A - Synthesis method for imidazo[1, 2-a]pyridine-3-phenyl ketone - Google Patents
Synthesis method for imidazo[1, 2-a]pyridine-3-phenyl ketone Download PDFInfo
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Abstract
The invention relates to a synthesis method for imidazo[1, 2-a]pyridine-3-phenyl ketone. The method includes: reacting N, N-dimethylformamide dimethylacetal with 2-aminopyridine at 40-100DEG C to obtain 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 the reaction, conducting cooling to room temperature, separating out high purity 6-chloroimidazo[1, 2-a]pyridine 3-phenyl ketone crystals, performing filtration, collecting filter cake, adding water into the mother solution, carrying out extraction, washing, drying and concentration to obtain a crude product, and recrystallizing the crude product to obtain a pure product. The method has the characteristics of easily available reaction raw materials, reasonable price, mild reaction condition, easy operation, easy control and simple aftertreatment, and the product has stable quality and high purity.
Description
(1) technical field
The invention belongs to organic synthesis field, be specifically related to the synthetic method of a kind of 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 1000L reactor, methyl tertiary butyl ether 237kg (8vol) is added, magnesium powder 9kg (1.8eq), drip containing main raw material 2, methyl tertiary butyl ether (4vol) the solution 159kg of 3-difluoro bromobenzene 40kg, be prepared into Grignard reagent 2,3-difluorophenyl magnesium bromide;
(2) in another 1000L reactor, methyl tertiary butyl ether 207kg (7vol) is added successively, Manganse Dioxide 1.8kg (0.1eq), aluminum chloride 2.7kg (0.1eq), butyryl oxide 82kg (2.5eq), temperature control 15 ± 2 DEG C drips above-mentioned Grignard reagent 2,3-difluorophenyl magnesium bromide, drips and finishes in this thermotonus 6h;
(3) reaction is finished, extraction, and the water washing of organic phase salt concentrates to obtain product 2,3-difluorobenzene butanone.
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.
Imidazo [1,2-a] pyridine-3-phenyl ketone is the important intermediate of organic synthesis as a kind of phenyl ketone derivative, 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 the synthetic method of a kind of 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 imidazo [1,2-a] pyridine-3-phenyl ketone, its special character is: comprise the following steps:
(1) N is prepared, N-dimethyl-N'-2-pyridyl-carbonamidine intermediate: DMF dimethylacetal and PA react obtained N, N-dimethyl-N'-2-pyridyl-carbonamidine intermediate at 40-100 DEG C;
(2) 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, have highly purified imidazo [1,2-a] pyridine 3-phenyl ketone crystal to separate out, suction filtration, collect filter cake, mother liquor adds water, and obtains imidazo [1 after extraction into ethyl acetate, water and saturated common salt water washing, anhydrous sodium sulfate drying, rotary evaporation concentrate, 2-a] the thick product of pyridine 3-phenyl ketone, this thick product recrystallization obtains sterling.
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, temperature described in step (1) is 40 DEG C, 60 DEG C, 80 DEG C, 100 DEG C.
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, reaction times 2-8 hour described in step (2).
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, the reaction times described in step (1) is 3 hours, 6 hours, 8 hours.
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, described in step (2), solvent is dioxane, toluene, DMF, at least one in N,N-dimethylacetamide.
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, 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 imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, temperature described in step (2) is 60 DEG C, 100 DEG C, 120 DEG C, 160 DEG C.
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, the reaction times described in step (2) is 3-15 hour.
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, the reaction times described in step (2) is 8 hours, 10 hours, 12 hours, 15 hours.
The synthetic method of imidazo of the present invention [1,2-a] pyridine-3-phenyl ketone, 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 PA (18.8g, 200mmol) 40 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-pyridyl-carbonamidine intermediate, rotary evaporation removes unnecessary DMF dimethylacetal, add 120 ml(125g) dioxane, NaHCO
3(25.2g, 300mmol) and alpha-fluoro ethyl ketone (59.7g, 300mmol), 100 DEG C are reacted 10 hours, reaction terminates, and is chilled to room temperature, is placed on refrigeration chamber 3 hours, suction filtration, obtains 14.6g high purity 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 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 12.1g, altogether 26.7g product, productive rate 60.13%, fusing point: 109.5-110.6 DEG C, 1HNMR (400MHz, DMSO) δ: 9.641 (d, J=6.8,1H), 8.238 (s, 1H), 7.873 (t, J=8Hz, 3H), 7.712-7.641 (m, 2H), 7.573 (t, J=7.6Hz, 2H), 7.330 (t, J=7.2Hz, 1H).
Embodiment 2
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, reacts 6 hours with at PA (18.8g, 200mmol) 80 DEG C, reaction terminates obtained N, N-dimethyl-N'-2 pyridyl-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 the highly purified imidazo of 17.6g [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 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 13.5g, altogether 31.1g product, productive rate 70.04%, fusing point: 109.5-110.6 DEG C, 1HNMR (400MHz, DMSO) δ: 9.641 (d, J=6.8,1H), 8.238 (s, 1H), 7.873 (t, J=8Hz, 3H), 7.712-7.641 (m, 2H), 7.573 (t, J=7.6Hz, 2H), 7.330 (t, J=7.2Hz, 1H).
Embodiment 3
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with PA (18.8g, 200mmol) reaction 3 hours at 100 DEG C, reaction terminates obtained N, N-dimethyl-N'-2 pyridyl-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 23g high purity 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 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 12.5g, altogether 35.5g product, productive rate 79.95%, fusing point: 109.5-110.6 DEG C, 1HNMR (400MHz, DMSO) δ: 9.641 (d, J=6.8,1H), 8.238 (s, 1H), 7.873 (t, J=8Hz, 3H), 7.712-7.641 (m, 2H), 7.573 (t, J=7.6Hz, 2H), 7.330 (t, J=7.2Hz, 1H).
7.532(t,J=8.0Hz,2H) 。
Embodiment 4
67ml(60.08g, 500mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with PA (18.8g, 200mmol) reaction 8 hours at 100 DEG C, reaction terminates obtained N, N-dimethyl-N'-2-(the fluoro-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 24.8g high purity 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 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 13g, altogether 37.8g product, productive rate 85.13%, fusing point: 109.5-110.6 DEG C, 1HNMR (400MHz, DMSO) δ: 9.641 (d, J=6.8,1H), 8.238 (s, 1H), 7.873 (t, J=8Hz, 3H), 7.712-7.641 (m, 2H), 7.573 (t, J=7.6Hz, 2H), 7.330 (t, J=7.2Hz, 1H).
Embodiment 5
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with PA (18.8g, 200mmol) reaction 8 hours at 60 DEG C, reaction terminates obtained N, N-dimethyl-N'-2 pyridyl-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 120 ml toluene, sodium carbonate (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 23g high purity 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 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 12.6g, altogether 35.6g product, fusing point: 109.5-110.7 DEG C, 1HNMR (400MH, DMSO) δ: 9.641 (d, J=6.8,1H), 8.238 (s, 1H), 7.873 (t, J=8Hz, 3H), 7.712-7.641 (m, 2H), 7.572 (t, J=7.5Hz, 2H), (7.331 t, J=7.2Hz, 1H).
7.53,0 (t,J=8.0Hz,2H) 。
Embodiment 6
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with PA (18.8g, 200mmol) reaction 7 hours at 80 DEG C, reaction terminates obtained N, N-dimethyl-N'-2 pyridyl-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 120 mlN, N-N,N-DIMETHYLACETAMIDE, saleratus (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 96 DEG C are reacted 10 hours, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 22.6g high purity 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 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 12.6g, altogether 35.2g product, fusing point: 109.5-110.5 DEG C.
Embodiment 7
80mL (71.7g, 600mmol) N, dinethylformamide dimethylacetal is solvent and reaction raw materials, with PA (18.8g, 200mmol) reaction 6 hours at 85 DEG C, reaction terminates obtained N, N-dimethyl-N'-2 pyridyl-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), 97 DEG C are reacted 10 hours, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 22.6g high purity 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 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 12.5g, altogether 35.1g product, fusing point: 109.5-110.5 DEG C.
Embodiment 8
350mmolN, dinethylformamide dimethylacetal is solvent and reaction raw materials, with PA (18.8g, 200mmol) reaction 0.5 hour at 102 DEG C, then 7ml toluene is added, salt of wormwood (0.5g) and alpha-brominated methyl phenyl ketone (5g) react 0.4 hour, reaction terminates obtained N, N-dimethyl-N'-2 pyridyl-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 220 ml toluene, salt of wormwood (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 110 DEG C are reacted 1 hour, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 23.4g high purity 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 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 12.6g, altogether 36g product, fusing point: 109.5-110.5 DEG C.
Embodiment 9
350mmolN, dinethylformamide dimethylacetal is solvent and reaction raw materials, with PA (18.8g, 200mmol) reaction 0.5 hour at 102 DEG C, then 7ml toluene is added, salt of wormwood (0.5g) and alpha-brominated methyl phenyl ketone (5g) react 0.4 hour, reaction terminates obtained N, N-dimethyl-N'-2 pyridyl-carbonamidine intermediate, rotary evaporation removes unnecessary N, dinethylformamide dimethylacetal, add 220 mlN, N-N,N-DIMETHYLACETAMIDE, salt of wormwood (300mmol) and alpha-brominated methyl phenyl ketone (59.7g, 300mmol), 165 DEG C are reacted 1 hour, reaction terminates, be chilled to room temperature, be placed on refrigeration chamber 3 hours, suction filtration, obtain 23.4g high purity 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 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 12.6g, altogether 36g product, fusing point: 109.5-110.5 DEG C.
Claims (10)
1. the synthetic method of 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-pyridyl-carbonamidine intermediate: DMF dimethylacetal and PA react obtained N, N-dimethyl-N'-2-pyridyl-carbonamidine intermediate at 40-100 DEG C;
(2) 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, have highly purified imidazo [1,2-a] pyridine 3-phenyl ketone crystal to separate out, suction filtration, collect filter cake, mother liquor adds water, and obtains imidazo [1 after extraction into ethyl acetate, water and saturated common salt water washing, anhydrous sodium sulfate drying, rotary evaporation concentrate, 2-a] the thick product of pyridine 3-phenyl ketone, this thick product recrystallization obtains sterling.
2. the synthetic method of imidazo according to claim 1 [1,2-a] pyridine-3-phenyl ketone, 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 imidazo according to claim 1 and 2 [1,2-a] pyridine-3-phenyl ketone, is characterized in that: reaction times 2-8 hour described in step (2).
4. the synthetic method of imidazo according to claim 3 [1,2-a] pyridine-3-phenyl ketone, is characterized in that: the reaction times described in step (1) is 3 hours, 6 hours, 8 hours.
5. the synthetic method of imidazo according to claim 1 and 2 [1,2-a] pyridine-3-phenyl ketone, 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 imidazo according to claim 1 and 2 [1,2-a] pyridine-3-phenyl ketone, 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 imidazo according to claim 1 and 2 [1,2-a] pyridine-3-phenyl ketone, 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 imidazo according to claim 1 and 2 [1,2-a] pyridine-3-phenyl ketone, is characterized in that: the reaction times described in step (2) is 3-15 hour.
9. the synthetic method of imidazo according to claim 8 [1,2-a] pyridine-3-phenyl ketone, 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 imidazo according to claim 1 and 2 [1,2-a] pyridine-3-phenyl ketone, 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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| 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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| 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 |
Non-Patent Citations (2)
| Title |
|---|
| IAN D. CUNNINGHAM ETAL: "Chemistry of Amidines. Part 1. Determination of the Site of Initial Protonation in N’-Pyridylformamidines", 《J. CHEM. SOC. PERKIN TRANS 2》 * |
| OMAR GOMEZ ETAL: "A revised approach to the synthesis of 3-acyl imidazo[1,2-a]pyridines", 《HETEROCYCLIC COMMUNICATIONS》 * |
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Application publication date: 20150819 |