Conditions | Yield |
---|---|
at 70℃; | 100% |
With sodium hydrogencarbonate In ethanol for 2h; Heating; | 90% |
In water; butan-1-ol at 130℃; for 12h; | 90% |
Conditions | Yield |
---|---|
With C46H48N6O5Pd; potassium acetate In N,N-dimethyl acetamide at 160℃; for 24h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 25℃; for 2h; Inert atmosphere; | 83% |
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 2h; Heating; | 72% |
Conditions | Yield |
---|---|
Stage #1: Bromoacetaldehyde diethyl acetal With hydrogenchloride In ethanol for 1.5h; Reflux; Stage #2: 2-aminopyridine With sodium hydrogencarbonate at 20℃; for 2h; pH=Ca. 7; | 62.2% |
Stage #1: Bromoacetaldehyde diethyl acetal With hydrogenchloride In water at 80℃; for 0.5h; Stage #2: 2-aminopyridine With sodium hydrogencarbonate In water at 20℃; for 2h; pH=7; | 55.9% |
With sodium carbonate In 1,4-dioxane; water for 22h; Cyclization; Tschitschibabin reaction; Heating; | 19% |
3,5-dibromoimidazo<1,2-a>pyridine
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 12h; Heating; | 34% |
With hydrazine hydrate In ethanol for 12h; Product distribution; Heating; various solvents and reaction conditions; |
5-bromo-3-nitroimidazo<1,2-a>pyridine
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 0.5h; Heating; | 20% |
With hydrazine hydrate In ethanol for 0.5h; Product distribution; Heating; various solvents and reaction conditions; |
5-chloro-2-pyridylamine
3-chloro-2-hydroxy-naphthalene-1,4-dione
A
imidazo[1,2-a]pyridine
B
2-chloro-6,11-dihydro-6,11-dioxo-naphtho-[2',3':4,5]imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With sodium bicarbonate; sodium chloride In 1,2-dimethoxyethane; dichloromethane; water | A n/a B 4% |
2,3-Dichloro-1,4-naphthoquinone
2-Amino-4-chloropyridine
A
imidazo[1,2-a]pyridine
B
10-chloro-5,6-dihydro-5,6-dioxonaphtho-[1',2':4,5]imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
In methanol; glycerol | A n/a B 2% |
Conditions | Yield |
---|---|
In water | A n/a B 2% |
Conditions | Yield |
---|---|
at 150 - 160℃; im Rohr; | |
Stage #1: 2-aminopyridine; 1-bromo-2,2-dimethoxyethane With hydrogenchloride In 1,4-dioxane; water Reflux; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water for 22h; Reflux; | |
Stage #1: 2-aminopyridine; 1-bromo-2,2-dimethoxyethane With hydrogenchloride In 1,4-dioxane; water Reflux; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water for 22h; Reflux; | |
Stage #1: 2-aminopyridine; 1-bromo-2,2-dimethoxyethane With hydrogenchloride In water Reflux; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water for 22h; Reflux; | |
Stage #1: 2-aminopyridine; 1-bromo-2,2-dimethoxyethane With hydrogenchloride In 1,4-dioxane; water Reflux; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water for 22h; Reflux; |
Conditions | Yield |
---|---|
at 200 - 210℃; im Rohr; | |
In ethanol Heating; |
2-Morpholinomethyl-1-(2-propynyl)-imidazole
A
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With perchloric acid; water 1.) MeOH, 5 h, reflux; Yield given. Multistep reaction. Yields of byproduct given; | |
With perchloric acid; water In methanol Mechanism; Product distribution; | |
With perchloric acid; water 1.) MeOH, 50 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given; |
1H-imidazo<1,2-a>pyridinium-8-carboxylate
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
at 250 - 270℃; for 4h; |
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III) | |
With lead(IV) acetate; benzene |
2-Amino-6-bromopyridine
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 79 percent / ethanol / 6 h / Heating 2: 90 percent / fuming nitric acid, conc. sulphuric acid 3: hydrazine hydrate / ethanol / 0.5 h / Heating; various solvents and reaction conditions View Scheme | |
Multi-step reaction with 3 steps 1: 79 percent / ethanol / 6 h / Heating 2: 80 percent / N-bromosuccinimide / CH2Cl2; CHCl3 / Ambient temperature 3: hydrazine hydrate / ethanol / 12 h / Heating; various solvents and reaction conditions View Scheme |
5-bromoimidazo<1,2-a>pyridine
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 90 percent / fuming nitric acid, conc. sulphuric acid 2: hydrazine hydrate / ethanol / 0.5 h / Heating; various solvents and reaction conditions View Scheme | |
Multi-step reaction with 2 steps 1: 80 percent / N-bromosuccinimide / CH2Cl2; CHCl3 / Ambient temperature 2: hydrazine hydrate / ethanol / 12 h / Heating; various solvents and reaction conditions View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 3.8 g / 0.08 h / 130 °C 2: 1.) aq. sodium hydroxide, 2.) aq. HCl / 1.) reflux, 3 - 4 h, 2.) heating, 10 min 3: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 4: 4 h / 250 - 270 °C View Scheme | |
Multi-step reaction with 5 steps 1: 3.8 g / 0.08 h / 130 °C 2: 8.3 g / aq. sodium hydroxide, hydrogen peroxide / ethanol / 1 h / 50 °C 3: 1.) aq. HCl, 2.) aq. sodium nitrite / 1.) 50 deg C, 1 h, 2.) 30 min, reflux 4: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 5: 4 h / 250 - 270 °C View Scheme | |
Multi-step reaction with 5 steps 1: 3.8 g / 0.08 h / 130 °C 2: 4.2 g / Ba(OH)2*8H2O / H2O / 4 h / Heating 3: 1.7 g / aq. HCl / H2O / 0.25 h / Heating 4: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 5: 4 h / 250 - 270 °C View Scheme |
N-(3-carboxy-2-pyridyl)aminoacetaldehyde
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 2: 4 h / 250 - 270 °C View Scheme |
N-(3-cyano-2-pyridyl)aminoacetaldehyde dimethyl acetal
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) aq. sodium hydroxide, 2.) aq. HCl / 1.) reflux, 3 - 4 h, 2.) heating, 10 min 2: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 3: 4 h / 250 - 270 °C View Scheme | |
Multi-step reaction with 4 steps 1: 8.3 g / aq. sodium hydroxide, hydrogen peroxide / ethanol / 1 h / 50 °C 2: 1.) aq. HCl, 2.) aq. sodium nitrite / 1.) 50 deg C, 1 h, 2.) 30 min, reflux 3: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 4: 4 h / 250 - 270 °C View Scheme | |
Multi-step reaction with 4 steps 1: 4.2 g / Ba(OH)2*8H2O / H2O / 4 h / Heating 2: 1.7 g / aq. HCl / H2O / 0.25 h / Heating 3: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 4: 4 h / 250 - 270 °C View Scheme |
N-(3-carboxamido-2-pyridyl)aminoacetaldehyde dimethyl acetal
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) aq. HCl, 2.) aq. sodium nitrite / 1.) 50 deg C, 1 h, 2.) 30 min, reflux 2: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 3: 4 h / 250 - 270 °C View Scheme |
N-(3-carboxy-2-pyridyl)aminoacetaldehyde dimethyl acetal
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.7 g / aq. HCl / H2O / 0.25 h / Heating 2: 0.9 g / sodium acetate, acetic anhydride / 0.5 h / Heating 3: 4 h / 250 - 270 °C View Scheme |
2-Morpholinomethyl-1-(2-propynyl)-imidazole
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) water, 2.) HClO4 / 1.) MeOH, 50 deg C, 2 h 2: 72 percent / aq. NaOH / methanol / 2 h / Heating View Scheme |
Conditions | Yield |
---|---|
With ammonia In methanol |
Conditions | Yield |
---|---|
With trichlorophosphate |
Conditions | Yield |
---|---|
at 160℃; for 14h; |
imidazo[1,2-a]pyridine
1-bromo-4-methoxy-benzene
3-(4-methoxylphenyl)imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere; | 100% |
With palladium 10% on activated carbon; potassium acetate In i-Amyl alcohol at 150℃; for 16h; Inert atmosphere; Green chemistry; | 93% |
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; | 80% |
imidazo[1,2-a]pyridine
4-bromobenzenecarbonitrile
4-(imidazo[1,2-a]pyridin-3-yl)benzonitrile
Conditions | Yield |
---|---|
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere; | 100% |
With sodium acetate In N,N-dimethyl acetamide at 166℃; for 12h; Inert atmosphere; Sonication; regioselective reaction; | 95% |
With palladium 10% on activated carbon; potassium acetate In N,N-dimethyl acetamide at 150℃; for 16h; Solvent; Inert atmosphere; | 94% |
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 80% |
imidazo[1,2-a]pyridine
para-bromoacetophenone
1-(4-(imidazo[1,2-a]pyridin-3-yl)phenyl)ethan-1-one
Conditions | Yield |
---|---|
With C26H22Cl2FN3OPd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Heck Reaction; Schlenk technique; Inert atmosphere; | 100% |
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere; | 100% |
With palladium 10% on activated carbon; potassium acetate In i-Amyl alcohol at 150℃; for 16h; Inert atmosphere; Green chemistry; | 96% |
With sodium acetate In N,N-dimethyl acetamide at 166℃; for 12h; Inert atmosphere; Sonication; regioselective reaction; | 94% |
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide Inert atmosphere; Schlenk technique; | 100% |
With C26H22Cl2FN3OPd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Reagent/catalyst; Heck Reaction; Schlenk technique; Inert atmosphere; | 99% |
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; | 58% |
With potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 160℃; for 1h; Microwave irradiation; Inert atmosphere; | 58% |
imidazo[1,2-a]pyridine
1,2-benzenedithiole
Conditions | Yield |
---|---|
at 5 - 8℃; Inert atmosphere; Glovebox; Sealed tube; Sonication; Green chemistry; | 100% |
imidazo[1,2-a]pyridine
3-methoxyphenyl bromide
3-(3-methoxyphenyl)imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With C27H22N4O2Pd; potassium acetate In N,N-dimethyl acetamide at 140℃; for 18h; Catalytic behavior; Schlenk technique; Inert atmosphere; | 100% |
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; | 53% |
imidazo[1,2-a]pyridine
1-tert-butyl-4-iodobenzene
Conditions | Yield |
---|---|
With sulfur; copper(l) iodide; potassium tert-butylate In acetic acid; N,N-dimethyl-formamide at 130℃; for 24h; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique; | 99% |
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium pivalate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; Schlenk technique; | 98% |
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With tert.-butylnitrite In acetonitrile at 70℃; for 0.25h; regioselective reaction; | 97% |
Conditions | Yield |
---|---|
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate at 150℃; for 16h; Inert atmosphere; Schlenk technique; | 96% |
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With sodium chloride In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With potassium iodate; glycerol In neat (no solvent) at 110℃; for 3h; Inert atmosphere; Schlenk technique; regioselective reaction; | 95% |
With ammonium iodide In acetonitrile at 20℃; for 18h; | 89% |
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 0.0833333h; regioselective reaction; | 88% |
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With iodine In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 95% |
imidazo[1,2-a]pyridine
3-bromoquinoline
3-(imidazo[1,2-a]pyridin-3-yl)quinoline
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; potassium acetate In i-Amyl alcohol at 150℃; for 16h; Inert atmosphere; Green chemistry; | 94% |
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 73% |
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; | 61% |
imidazo[1,2-a]pyridine
3-cyanobromobenzene
3-(imidazo[1,2-a]pyridin-2-yl)benzonitrile
Conditions | Yield |
---|---|
With sodium acetate In N,N-dimethyl acetamide at 166℃; for 12h; Inert atmosphere; Sonication; regioselective reaction; | 94% |
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 93% |
imidazo[1,2-a]pyridine
thiophenol
3-(phenylthio)imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
Stage #1: thiophenol With N-chloro-succinimide In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: imidazo[1,2-a]pyridine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; regioselective reaction; | 94% |
With rose bengal In dimethyl sulfoxide for 6h; Irradiation; Molecular sieve; regioselective reaction; | 85% |
With 5-ethyl-10-(2-hydroxylethyl)-7,8-dimethylisoalloxazinium triflate; iodine; oxygen In acetonitrile at 50℃; under 760.051 Torr; for 16h; Green chemistry; chemoselective reaction; | 70% |
imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With iodine In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran for 12h; Acetylation; Heating; | 93% |
Conditions | Yield |
---|---|
With palladium(II) complex with imidazolyl carbene ligandO; cesium acetate In N,N-dimethyl acetamide at 125℃; for 24h; | 93% |
With cobalt(II) chloride hexahydrate; potassium acetate In N,N-dimethyl-formamide at 150℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; | 92% |
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; | 65% |
imidazo[1,2-a]pyridine
4-methoxycarbonylphenyl bromide
methyl 4-(imidazo[1,2-a]pyridin-3-yl)benzoate
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
With oxygen; copper diacetate; acetic acid In toluene at 140℃; for 12h; Schlenk technique; Sealed tube; regioselective reaction; | 93% |
Conditions | Yield |
---|---|
With sulfur; copper(l) iodide; potassium tert-butylate In acetic acid; N,N-dimethyl-formamide at 130℃; for 24h; Sealed tube; | 93% |
3-Bromopyridine
imidazo[1,2-a]pyridine
3-(pyridin-3-yl)imidazo[1,2-a]pyridine
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 92% |
With potassium carbonate; triphenylphosphine; palladium diacetate In 1,4-dioxane; ethanol at 130℃; for 1h; microwave irradiation; | 90% |
imidazo[1,2-a]pyridine
o-cyanobromobenzene
2-(imidazo[1,2-a]pyridin-3-yl)benzonitrile
Conditions | Yield |
---|---|
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere; | 92% |
With palladium 10% on activated carbon; potassium acetate In pentan-1-ol at 150℃; for 16h; Solvent; Inert atmosphere; Green chemistry; | 92% |
Conditions | Yield |
---|---|
With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; | 92% |
With NHC-Pd(II)-Im; sodium t-butanolate In tetrahydrofuran at 120℃; for 12h; Reagent/catalyst; Solvent; Inert atmosphere; | 92% |
With palladium diacetate; potassium hydroxide In water at 100℃; for 24h; Inert atmosphere; | 54% |
The Imidazo[1,2-a]pyridine is an organic compound with the formula C7H6N2. The IUPAC name of this chemical is imidazo[1,2-a]pyridine. With the CAS registry number 274-76-0, it is also named as H-imidazo[1,2-a]pyridine. The product's categories are C7 and C8; Heterocyclic Building Blocks; Pyridines. Besides, it should be stored in a cool, dry place.
Physical properties about Imidazo[1,2-a]pyridine are: (1)ACD/LogP: 1.49; (2)ACD/LogD (pH 5.5): 0.193; (3)ACD/LogD (pH 7.4): 1.391; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 6.366; (6)ACD/KOC (pH 5.5): 7.795; (7)ACD/KOC (pH 7.4): 122.883; (8)#H bond acceptors: 2 ; (9)Polar Surface Area: 17.3 Å2; (10)Index of Refraction: 1.628; (11)Molar Refractivity: 36.713 cm3; (12)Molar Volume: 103.418 cm3; (13)Polarizability: 14.554×10-24cm3; (14)Surface Tension: 45.705 dyne/cm; (15)Density: 1.142 g/cm3.
Preparation: this chemical can be prepared by pyridin-2-ylamine and chloroacetaldehyde. This reaction will need reagent sodium bicarbonate and solvent H2O. The reaction time is 72 hours at ambient temperature.
Uses of Imidazo[1,2-a]pyridine: it can be used to produce 2,2,2-trichloro-1-imidazo[1,2-a]pyridin-3-yl-ethanol at ambient temperature. It will need solvent benzene. The yield is about 83%.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: c1ccn2ccnc2c1
(2)InChI: InChI=1/C7H6N2/c1-2-5-9-6-4-8-7(9)3-1/h1-6H
(3)InChIKey: UTCSSFWDNNEEBH-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C7H6N2/c1-2-5-9-6-4-8-7(9)3-1/h1-6H
(5)Std. InChIKey: UTCSSFWDNNEEBH-UHFFFAOYSA-N
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