CN104557922A - Synthetic method for 6-bromoimidazo[1,2-a]pyridine-8-carboxylic acid - Google Patents
Synthetic method for 6-bromoimidazo[1,2-a]pyridine-8-carboxylic acid Download PDFInfo
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- CN104557922A CN104557922A CN201410846459.3A CN201410846459A CN104557922A CN 104557922 A CN104557922 A CN 104557922A CN 201410846459 A CN201410846459 A CN 201410846459A CN 104557922 A CN104557922 A CN 104557922A
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- 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 belongs to the field of organic synthesis and particularly relates to a synthetic method for 6-bromoimidazo[1,2-a]pyridine-8-carboxylic acid. The method comprises the following steps: reacting 2-aminonicotinic acid with N-bromobutanimide at subzero 8-35 DEG C in the presence of a solvent in proportion, reacting with chloroacetaldehyde at 30-130 DEG C, adding alkali, dropwise adding concentrated hydrochloric acid until the pH value is 3-6, and obtaining a crude product, wherein cotton-wool-shaped materials are generated in the dropwise-adding process; re-crystallizing by water and ethanol in proportion to obtain a pure product. The reaction raw materials are easily available and reasonable in price; the method is mild in reaction condition, easy to carry out and simple in post-treatment; moreover, 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 6-bromine imidazo [1,2-a] pyridine-8-formic acid.
(2) background technology
6-bromine imidazo [1,2-a] pyridine-8-formic acid 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 medicine intermediate is more novel, has very large using value.
Disclose a kind of synthetic method of 6-bromine imidazo [1,2-a] pyridine-3-formic acid in August 6 in 2014, comprise the following steps:
N, N-dimethylformamide dimethyl and 2-amino-5-bromopyridine react at 40-100 DEG C, under alkali effect, in certain solvent, react at 60-160 DEG C with ethyl bromoacetate, then under alkali effect, hydrolysis reaction 1-5 hour, reaction terminates, neutralize through hydrochloric acid, filter, wash, dry direct must 6-bromine imidazo [1,2-a] pyridine-3-formic acid sterling.
(3) summary of the invention
The present invention is in order to make up the deficiencies in the prior art, and provide the synthetic method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid, 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-8-formic acid, its special character is: comprise the following steps:
(1) 2-amino-nicotinic acid and N-bromo-succinimide are in certain ratio, at certain solvent, react under subzero 8-35 degree Celsius, obtained 2-amino-5-bromo-nicotinic acid, and this intermediate does not need to purify;
(2) react at 30-130 DEG C generates 6-bromine imidazo [1,2-a] pyridine-8-formic acid with a certain proportion of monochloroacetaldehyde. hydrochloride, reaction terminates, and is down to room temperature, then puts into refrigerator and continues to lower the temperature, product precipitation, the thick product of low temperature suction filtration;
(3) this thick product water dissolves add alkali completely, then drips concentrated hydrochloric acid to pH value to 3-6, has flocculence produce raw, obtain crude product in dropping process; Use the sterling of water and ethanol certain proportion recrystallization again.
The preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid of the present invention, said solvent is ethyl acetate, ethanol, DMF, acetonitrile and N,N-dimethylacetamide.
The preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid of the present invention, said alkali is saleratus, salt of wormwood, sodium bicarbonate, sodium carbonate.
The preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid of the present invention, said proper temperature is 40 DEG C, 50 DEG C, 60,70 DEG C and 80 DEG C.
The preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid of the present invention, the certain proportion of said 2-amino-nicotinic acid and N-bromo-succinimide refers to 1:1.05,1:1.1,1:1.15,1:1.2,1:1.25.
The preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid of the present invention, said 2-amino-5-bromo-nicotinic acid and monochloroacetaldehyde certain proportion are 1:1,1:1.15,1:1.2,1:1.25,1:3.
The preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid of the present invention, the certain proportion of said water and ethanol is 1:1,1.5:1,2:1,1:1.5,1:2.
The preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid of the present invention, step (1) reaction times is 3-10 hour, and step (1) reaction times is 6-12 hour.
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
2-amino-nicotinic acid (20.7g, 150mmol) and N-bromo-succinimide (28.04g, 157.5mmol) make solvent by ethyl acetate, react 6 hours under subzero 5-10 degree Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary solvent, adds the aqueous chloroacetaldehyde solution of 165mmol (32.38g) 40%, and 40 DEG C are reacted 10 hours, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated potassium bicarbonate aqueous solution, then drip concentrated hydrochloric acid, regulate pH value to 3-6, have flocculence produce raw in dropping process, dropwise latter standing 6 hours, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 1:1 and obtain sterling 22.85g, productive rate 63.2%, fusing point: 110.5-112.0 DEG C, nuclear magnetic resonance spectroscopy:
1HNMR(400MHzCDCl3):11.0(s,1H),8.87(s,1H),7.62(d,J=8.0Hz,1H),7.48(s,1H), 7.37(q,J=8.0Hz,2H)。
Embodiment 2
2-amino-nicotinic acid (27.6g, 200mmol) and N-bromo-succinimide (NBS) (39.16g, 220mmol) ethanol as solvent, react 3 hours under subzero 8 degrees Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary etoh solvent, adds the aqueous chloroacetaldehyde solution of 230mmol (45.14g) 40%, and 50 DEG C are reacted 6 hours, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated wet chemical, then drip concentrated hydrochloric acid, regulate pH value to 3-6, have flocculence produce raw in dropping process, dropwise latter standing 6 hours, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 1:1.5 and obtain sterling 39.38g, productive rate 81.7%, fusing point: 110.5-112.0 DEG C, nuclear magnetic resonance spectroscopy:
1HNMR(400MHzCDCl3):11.0(s,1H),8.87(s,1H),7.62(d,J=8.0Hz,1H),7.48(s,1H), 7.37(q,J=8.0Hz,2H)。
Embodiment 3
2-amino-nicotinic acid (27.6g, 200mmol) and N-bromo-succinimide (NBS) (40.94g, 230mmol) make solvent with DMF, react 10 hours under subzero 35 degrees Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary solvent, adds the aqueous chloroacetaldehyde solution of 240mmol (47.10g) 40%, and 60 DEG C are reacted 12 hours, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated sodium bicarbonate aqueous solution, then drip concentrated hydrochloric acid, regulate pH value to 3-6, have flocculence produce raw in dropping process, dropwise latter standing 6 hours, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 2:1 and obtain sterling 40.10g, productive rate 83.2%, fusing point: 110.5-112.0 DEG C, nuclear magnetic resonance spectroscopy:
1HNMR(400MHzCDCl3):11.0(s,1H),8.87(s,1H),7.62(d,J=8.0Hz,1H),7.48(s,1H), 7.37(q,J=8.0Hz,2H)。
Embodiment 4
2-amino-nicotinic acid (27.6g, 200mmol) and N-bromo-succinimide (NBS) (42.72g, 240mmol) acetonitrile as solvents, react 7 hours under subzero 15 degrees Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary etoh solvent, adds the aqueous chloroacetaldehyde solution of 250mmol (49.06g) 40%, and 70 DEG C are reacted 11 hours, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated aqueous sodium carbonate, then drip concentrated hydrochloric acid, regulate pH value to 3-6, have flocculence produce raw in dropping process, dropwise latter standing 6 hours, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 1.5:1 and obtain sterling 36.44g, productive rate 75.6 %, fusing point: 110.5-112.0 DEG C, nuclear magnetic resonance spectroscopy:
1HNMR(400MHzCDCl3):11.0(s,1H),8.87(s,1H),7.62(d,J=8.0Hz,1H),7.48(s,1H), 7.37(q,J=8.0Hz,2H)。
Embodiment 5
2-amino-nicotinic acid (27.6g, 200mmol) and N-bromo-succinimide (NBS) (44.50g, 250mmol) make solvent by N,N-dimethylacetamide, react 6 hours under subzero 10 degrees Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary solvent, adds the aqueous chloroacetaldehyde solution of 260mmol (51.03g) 40%, and 80 DEG C are reacted 10 hours, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated aqueous sodium carbonate, then drip concentrated hydrochloric acid, regulate pH value to 3-6, have flocculence produce raw in dropping process, dropwise latter standing 6 hours, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 1:2 and obtain sterling 26.64g, productive rate 55.27%, fusing point: 110.5-112.0 DEG C, nuclear magnetic resonance spectroscopy:
1HNMR(400MHzCDCl3):11.0(s,1H),8.87(s,1H),7.62(d,J=8.0Hz,1H),7.48(s,1H), 7.37(q,J=8.0Hz,2H)。
Embodiment 6
2-amino-nicotinic acid (27.6g, 200mmol) and N-bromo-succinimide (NBS) (44.50g, 250mmol) make solvent by N,N-dimethylacetamide, react 6 hours under subzero 10 degrees Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary solvent, adds the aqueous chloroacetaldehyde solution of 260mmol (51.03g) 40%, and 130 DEG C are reacted 8 hours, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated aqueous sodium carbonate, then drip concentrated hydrochloric acid, regulate pH value to 3-6, have flocculence produce raw in dropping process, dropwise latter standing 6 hours, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 1:1 and obtain sterling 35.09g, productive rate 72.8%, fusing point: 110.5-112.0 DEG C, nuclear magnetic resonance spectroscopy:
1HNMR(400MHzCDCl3):11.0(s,1H),8.87(s,1H),7.62(d,J=8.0Hz,1H),7.48(s,1H), 7.37(q,J=8.0Hz,2H)。
Embodiment 7
2-amino-nicotinic acid (27.6g, 200mmol) and N-bromo-succinimide (44.50g, 250mmol) make solvent by N,N-dimethylacetamide, react 6 hours under subzero 10 degrees Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary solvent, adds the aqueous chloroacetaldehyde solution of 260mmol (51.03g) 40%, and 30 DEG C are reacted 11 hours, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated aqueous sodium carbonate, then drip concentrated hydrochloric acid, regulate pH value to 3-6, have flocculence produce raw in dropping process, dropwise latter standing 6 hours, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 1:1.8 and obtain sterling 35.57g, productive rate 73.8%.
Embodiment 8
2-amino-nicotinic acid (27.6g, 200mmol) and N-bromo-succinimide (44.50g, 250mmol) N, N-N,N-DIMETHYLACETAMIDE makes solvent, 5ml water first reacts 5min at normal temperatures, then reacts 0.5 hour under subzero 15 degrees Celsius, obtained 2-amino-5-bromo-nicotinic acid; Rotary evaporation removes unnecessary solvent, adds the aqueous chloroacetaldehyde solution of 100g40%, and 100 DEG C are reacted 0.8 hour, and reaction terminates, and be chilled to room temperature, then put into refrigerator and continue cooling 4 hours, cold-draw filters to obtain crude product.Dissolve crude product with saturated aqueous sodium carbonate, then drip concentrated hydrochloric acid, regulate pH value to 3, have flocculence produce raw in dropping process, after dropwising, add water and ethanol 1:1.8 mixed solution 8ml leaves standstill 0.5 hour, suction filtration, washs to obtain crude product.Carry out recrystallization with water and ethanol 1:1.8 and obtain sterling 43.48g, productive rate 90.2%.
Claims (8)
1. the synthetic method of 6-bromine imidazo [1, a 2-a] pyridine-8-formic acid, is characterized in that: comprise the following steps:
(1) 2-amino-nicotinic acid and N-bromo-succinimide are in certain ratio, at certain solvent, react under subzero 8-35 degree Celsius, obtained 2-amino-5-bromo-nicotinic acid, and this intermediate does not need to purify;
(2) react at 30-130 DEG C generates 6-bromine imidazo [1,2-a] pyridine-8-formic acid with a certain proportion of monochloroacetaldehyde. hydrochloride, reaction terminates, and is down to room temperature, then puts into refrigerator and continues to lower the temperature, product precipitation, the thick product of low temperature suction filtration;
(3) this thick product water dissolves add alkali completely, then drips concentrated hydrochloric acid to pH value to 3-6, has flocculence produce raw, obtain crude product in dropping process; Use the sterling of water and ethanol certain proportion recrystallization again.
2. the preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid according to claim 1, is characterized in that: said solvent is ethyl acetate, ethanol, DMF, acetonitrile and N,N-dimethylacetamide.
3. the preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid according to claim 1 and 2, is characterized in that: said alkali is saleratus, salt of wormwood, sodium bicarbonate, sodium carbonate.
4. the preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid according to claim 1 and 2, is characterized in that: said proper temperature is 40 DEG C, 50 DEG C, 60,70 DEG C and 80 DEG C.
5. the preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid according to claim 1 and 2, is characterized in that: the certain proportion of said 2-amino-nicotinic acid and N-bromo-succinimide refers to 1:1.05,1:1.1,1:1.15,1:1.2,1:1.25.
6. the preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid according to claim 1 and 2, is characterized in that: said 2-amino-5-bromo-nicotinic acid and monochloroacetaldehyde certain proportion are 1:1,1:1.15,1:1.2,1:1.25,1:3.
7. the preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid according to claim 1 and 2, is characterized in that: the certain proportion of said water and ethanol is 1:1,1.5:1,2:1,1:1.5,1:2.
8. the preparation method of 6-bromine imidazo [1,2-a] pyridine-8-formic acid according to claim 1 and 2, it is characterized in that: step (1) reaction times is 3-10 hour, step (1) reaction times is 6-12 hour.
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Cited By (1)
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| CN104892603A (en) * | 2015-06-17 | 2015-09-09 | 山东国润生物医药有限公司 | Synthetic method for 6-iodo-imidazo [1,2-a] pyridine-8-formic acid |
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Application publication date: 20150429 |