Product Name

  • Name

    Imidazo[1,2-a]pyridine

  • EINECS
  • CAS No. 274-76-0
  • Article Data48
  • CAS DataBase
  • Density 1.142 g/cm3
  • Solubility
  • Melting Point
  • Formula C7H6N2
  • Boiling Point 103oC (1 mmHg)
  • Molecular Weight 118.138
  • Flash Point 113oC
  • Transport Information
  • Appearance
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 274-76-0 (Imidazo[1,2-a]pyridine)
  • Hazard Symbols IrritantXi
  • Synonyms 1,3a-Diazaindene;1-Azaindolizine;Pyridino[1',2':1,2]glyoxaline;Pyrimidazole;
  • PSA 17.30000
  • LogP 1.33430

Synthetic route

2-aminopyridine
504-29-0

2-aminopyridine

2-chloroethanal
107-20-0

2-chloroethanal

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
at 70℃;100%
With sodium hydrogencarbonate In ethanol for 2h; Heating;90%
In water; butan-1-ol at 130℃; for 12h;90%
imidazo[1,2-a]pyridine-3-carboxylic acid
6200-60-8

imidazo[1,2-a]pyridine-3-carboxylic acid

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With C46H48N6O5Pd; potassium acetate In N,N-dimethyl acetamide at 160℃; for 24h; Inert atmosphere;99%
3-bromoimidazo[1,2-a]pyridine
4926-47-0

3-bromoimidazo[1,2-a]pyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With sodium tetrahydroborate; N,N,N,N,-tetramethylethylenediamine; palladium diacetate; triphenylphosphine In tetrahydrofuran at 25℃; for 2h; Inert atmosphere;83%
7,7-(3-Oxa-1,5-pentanediyl)-7,8-dihydroimidazo<1,2-a>pyrazinium perchlorate

7,7-(3-Oxa-1,5-pentanediyl)-7,8-dihydroimidazo<1,2-a>pyrazinium perchlorate

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With sodium hydroxide In methanol for 2h; Heating;72%
2-aminopyridine
504-29-0

2-aminopyridine

Bromoacetaldehyde diethyl acetal
2032-35-1

Bromoacetaldehyde diethyl acetal

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
69214-12-6

3,5-dibromoimidazo<1,2-a>pyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
111753-05-0

5-bromo-3-nitroimidazo<1,2-a>pyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
1072-98-6

5-chloro-2-pyridylamine

3-chloro-2-hydroxy-naphthalene-1,4-dione
1526-73-4

3-chloro-2-hydroxy-naphthalene-1,4-dione

A

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

B

2-chloro-6,11-dihydro-6,11-dioxo-naphtho-[2',3':4,5]imidazo[1,2-a]pyridine
192654-05-0

2-chloro-6,11-dihydro-6,11-dioxo-naphtho-[2',3':4,5]imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With sodium bicarbonate; sodium chloride In 1,2-dimethoxyethane; dichloromethane; waterA n/a
B 4%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

2-Amino-4-chloropyridine
19798-80-2

2-Amino-4-chloropyridine

A

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

B

10-chloro-5,6-dihydro-5,6-dioxonaphtho-[1',2':4,5]imidazo[1,2-a]pyridine
192654-11-8

10-chloro-5,6-dihydro-5,6-dioxonaphtho-[1',2':4,5]imidazo[1,2-a]pyridine

Conditions
ConditionsYield
In methanol; glycerolA n/a
B 2%
1,2-dihydro-1,2-dioxo-4-sulfonate of potassium naphthalene

1,2-dihydro-1,2-dioxo-4-sulfonate of potassium naphthalene

2-amino-5-fluoropyridine
21717-96-4

2-amino-5-fluoropyridine

A

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

B

5,6-Dihydro-5,6-dioxo-5-fluoro-naphtho[1',2':4,5]imidazo[1,2-a] pyridine

5,6-Dihydro-5,6-dioxo-5-fluoro-naphtho[1',2':4,5]imidazo[1,2-a] pyridine

Conditions
ConditionsYield
In waterA n/a
B 2%
2-aminopyridine
504-29-0

2-aminopyridine

1-bromo-2,2-dimethoxyethane
7252-83-7

1-bromo-2,2-dimethoxyethane

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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;
2-aminopyridine
504-29-0

2-aminopyridine

bromoacetaldehyde
17157-48-1

bromoacetaldehyde

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
at 200 - 210℃; im Rohr;
In ethanol Heating;
2-Morpholinomethyl-1-(2-propynyl)-imidazole
85102-38-1

2-Morpholinomethyl-1-(2-propynyl)-imidazole

A

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

B

7,7-(3-Oxa-1,5-pentanediyl)-7,8-dihydroimidazo<1,2-a>pyrazinium perchlorate

7,7-(3-Oxa-1,5-pentanediyl)-7,8-dihydroimidazo<1,2-a>pyrazinium perchlorate

Conditions
ConditionsYield
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
74149-50-1

1H-imidazo<1,2-a>pyridinium-8-carboxylate

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
at 250 - 270℃; for 4h;
2,3-dihydro-imidazole<1,2-α>pyridine

2,3-dihydro-imidazole<1,2-α>pyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With water; sodium hydrogencarbonate; potassium hexacyanoferrate(III)
With lead(IV) acetate; benzene
2-Amino-6-bromopyridine
19798-81-3

2-Amino-6-bromopyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
69214-09-1

5-bromoimidazo<1,2-a>pyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
74149-49-8

N-(3-carboxy-2-pyridyl)aminoacetaldehyde

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
74149-44-3

N-(3-cyano-2-pyridyl)aminoacetaldehyde dimethyl acetal

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
74149-47-6

N-(3-carboxamido-2-pyridyl)aminoacetaldehyde dimethyl acetal

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
74149-46-5

N-(3-carboxy-2-pyridyl)aminoacetaldehyde dimethyl acetal

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
85102-38-1

2-Morpholinomethyl-1-(2-propynyl)-imidazole

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
2-aminopyridine
504-29-0

2-aminopyridine

aqueous chloroacetaldehyde

aqueous chloroacetaldehyde

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With ammonia In methanol
2-chloropyridine
109-09-1

2-chloropyridine

5-chloro-2-pyridylamine
1072-98-6

5-chloro-2-pyridylamine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With trichlorophosphate
1,2,3-triazole
288-36-8

1,2,3-triazole

2-bromo-pyridine
109-04-6

2-bromo-pyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Conditions
ConditionsYield
at 160℃; for 14h;
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

3-(4-methoxylphenyl)imidazo[1,2-a]pyridine
1338248-76-2

3-(4-methoxylphenyl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-(imidazo[1,2-a]pyridin-3-yl)benzonitrile
59182-08-0

4-(imidazo[1,2-a]pyridin-3-yl)benzonitrile

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

para-bromoacetophenone
99-90-1

para-bromoacetophenone

1-(4-(imidazo[1,2-a]pyridin-3-yl)phenyl)ethan-1-one
59182-04-6

1-(4-(imidazo[1,2-a]pyridin-3-yl)phenyl)ethan-1-one

Conditions
ConditionsYield
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%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

bromobenzene
108-86-1

bromobenzene

3-phenylimidazo[1,2-a]pyridine
92961-15-4

3-phenylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

1,2-benzenedithiole
17534-15-5

1,2-benzenedithiole

imidazolium[1,2-a]pyridine benzene 1-thiol 2-thiolate

imidazolium[1,2-a]pyridine benzene 1-thiol 2-thiolate

Conditions
ConditionsYield
at 5 - 8℃; Inert atmosphere; Glovebox; Sealed tube; Sonication; Green chemistry;100%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

3-methoxyphenyl bromide
2398-37-0

3-methoxyphenyl bromide

3-(3-methoxyphenyl)imidazo[1,2-a]pyridine
1338248-69-3

3-(3-methoxyphenyl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

1-tert-butyl-4-iodobenzene
35779-04-5

1-tert-butyl-4-iodobenzene

2,3-bis((4-tert-butylphenyl)thio)imidazo[1,2-a]pyridine

2,3-bis((4-tert-butylphenyl)thio)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With sulfur; copper(l) iodide; potassium tert-butylate In acetic acid; N,N-dimethyl-formamide at 130℃; for 24h; Sealed tube;99%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

3-(p-tolylthio)imidazo[1,2-a]pyridine

3-(p-tolylthio)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique;99%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

1-benzyl-5-(2-bromophenyl)tetrazole

1-benzyl-5-(2-bromophenyl)tetrazole

3-(2-(1-benzyltetrazol-5-yl)phenyl)imidazo[1,2-a]pyridine

3-(2-(1-benzyltetrazol-5-yl)phenyl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

3-nitrosoimidazo[1,2-a]pyridine

3-nitrosoimidazo[1,2-a]pyridine

Conditions
ConditionsYield
With tert.-butylnitrite In acetonitrile at 70℃; for 0.25h; regioselective reaction;97%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

3-([1,1'-biphenyl]-2-yl)imidazo[1,2-a]pyridine

3-([1,1'-biphenyl]-2-yl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With PdCl(1,4-bis(diphenylphosphino)butane)(C3H5); potassium acetate at 150℃; for 16h; Inert atmosphere; Schlenk technique;96%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

2-((difluoromethyl)thio)isoindoline-1,3-dione

2-((difluoromethyl)thio)isoindoline-1,3-dione

3-[(difluoromethyl)thio]-imidazo[1,2-a]pyridine

3-[(difluoromethyl)thio]-imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With sodium chloride In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique; Inert atmosphere;95%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

diphenyl diselenide
1666-13-3

diphenyl diselenide

3-(phenylselanyl)imidazo[1,2-a]pyridine

3-(phenylselanyl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

sodium S-(6-chloro-1H-indol-3-yl) thiosulfate

sodium S-(6-chloro-1H-indol-3-yl) thiosulfate

3-((6-chloro-1H-indol-3-yl)thio)imidazo[1,2-a]pyridine

3-((6-chloro-1H-indol-3-yl)thio)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;95%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

1-bromo-4-(trifluoromethoxy)benzene
407-14-7

1-bromo-4-(trifluoromethoxy)benzene

3-(4-(trifluoromethoxy)phenyl)imidazo[1,2-a]pyridine

3-(4-(trifluoromethoxy)phenyl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;95%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

3-bromoquinoline
5332-24-1

3-bromoquinoline

3-(imidazo[1,2-a]pyridin-3-yl)quinoline
1373494-56-4

3-(imidazo[1,2-a]pyridin-3-yl)quinoline

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

3-(imidazo[1,2-a]pyridin-2-yl)benzonitrile
1373494-46-2

3-(imidazo[1,2-a]pyridin-2-yl)benzonitrile

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

thiophenol
108-98-5

thiophenol

3-(phenylthio)imidazo[1,2-a]pyridine
1609583-33-6

3-(phenylthio)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

sodium 4-bromobenzylsulfanesulfonate

sodium 4-bromobenzylsulfanesulfonate

3-((4-bromobenzyl)thio)imidazo[1,2-a]pyridine

3-((4-bromobenzyl)thio)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With iodine In dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere; regioselective reaction;94%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

Trichloroacetyl chloride
76-02-8

Trichloroacetyl chloride

3-(trichloroacetyl)imidazo[1,2-a]pyridine

3-(trichloroacetyl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With dmap In tetrahydrofuran for 12h; Acetylation; Heating;93%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

iodobenzene
591-50-4

iodobenzene

3-phenylimidazo[1,2-a]pyridine
92961-15-4

3-phenylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

methyl 4-(imidazo[1,2-a]pyridin-3-yl)benzoate
1373494-42-8

methyl 4-(imidazo[1,2-a]pyridin-3-yl)benzoate

Conditions
ConditionsYield
With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 150℃; for 16h; Inert atmosphere;93%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

1-dodecylthiol
112-55-0

1-dodecylthiol

C19H30N2S

C19H30N2S

Conditions
ConditionsYield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction;93%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

4-ethylacetophenone
937-30-4

4-ethylacetophenone

1-(4-ethylphenyl)-2-(imidazo[1,2-a]pyridin-3-yl)ethane-1,2-dione

1-(4-ethylphenyl)-2-(imidazo[1,2-a]pyridin-3-yl)ethane-1,2-dione

Conditions
ConditionsYield
With oxygen; copper diacetate; acetic acid In toluene at 140℃; for 12h; Schlenk technique; Sealed tube; regioselective reaction;93%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

4-fluoro-1-iodobenzene
352-34-1

4-fluoro-1-iodobenzene

2,3-bis((4-fluorophenyl)thio)imidazo[1,2-a]pyridine

2,3-bis((4-fluorophenyl)thio)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
With sulfur; copper(l) iodide; potassium tert-butylate In acetic acid; N,N-dimethyl-formamide at 130℃; for 24h; Sealed tube;93%
3-Bromopyridine
626-55-1

3-Bromopyridine

imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

3-(pyridin-3-yl)imidazo[1,2-a]pyridine
930113-28-3

3-(pyridin-3-yl)imidazo[1,2-a]pyridine

Conditions
ConditionsYield
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
274-76-0

imidazo[1,2-a]pyridine

o-cyanobromobenzene
2042-37-7

o-cyanobromobenzene

2-(imidazo[1,2-a]pyridin-3-yl)benzonitrile
1373494-50-8

2-(imidazo[1,2-a]pyridin-3-yl)benzonitrile

Conditions
ConditionsYield
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%
imidazo[1,2-a]pyridine
274-76-0

imidazo[1,2-a]pyridine

chlorobenzene
108-90-7

chlorobenzene

3-phenylimidazo[1,2-a]pyridine
92961-15-4

3-phenylimidazo[1,2-a]pyridine

Conditions
ConditionsYield
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%

Imidazo[1,2-a]pyridine Specification

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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