6188-23-4

Basic information

• Product Name: 6-Bromoimidazo[1,2-a]pyridine
• Synonyms: BUTTPARK 154\50-43;6-BROMOIMIDAZO[1,2-A]PYRIDINE;6-BROMO-INIDAZO[1,2-A]-PYRIDINE;6- BROMINE IMIDAZOLYL [ 1,2-A ] PYRIDINE;6-Bromoimidazo[1,2-a]pyri...;6-BroMoiMidazolo[1,2-a]pyridine;IMidazo[1,2-a]pyridine, 6-broMo-;6-BroMo IMidazole[1,2-a]Pyridine
• CAS NO: 6188-23-4
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.03
• EINECS: 1592732-453-0
• Product Categories: blocks;Bromides;Imidazoles;Pyridines;CHIRAL CHEMICALS;Building Blocks;Imidazo[x,x-y]pyridine;Heterocycle-Pyridine series
• Mol File: 6188-23-4.mol
• Article Data: 35

Chemical Properties

• Melting Point: 76-78 °C
• Boiling Point: 165 °C(Press: 1.5 Torr)
• Appearance: /
• Density: 1.69 g/cm³
• Refractive Index: 1.688
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 5.10±0.50(Predicted)
• Water Solubility: slightly soluble in water.
• CAS DataBase Reference: 6-Bromoimidazo[1,2-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoimidazo[1,2-a]pyridine(6188-23-4)
• EPA Substance Registry System: 6-Bromoimidazo[1,2-a]pyridine(6188-23-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6188-23-4(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

It is used in organic syntheses and as pharmaceutical intermediates. The best results were obtained with lactams that could be introduced on the 6-bromoimidazo[1,2-a]pyridine. 1,2-dihydro-5-imidazo [1,2-a]pyridin-6-yl-6-methyl-2-oxo-3-pyridinecarbonitrile hydrochloride monohydrate 6 was synthesized in 5 steps from 6-bromoimidazo[1,2-a] pyridine using [2- 14 C] cyanoacetamide as the source of the radiolabel.

InChI:InChI=1/C7H5BrN2/c8-6-1-2-7-9-3-4-10(7)5-6/h1-5H

Synthetic route

2-chloroethanal (107-20-0) + 5-bromo-2-pyridylamine (1072-97-5) → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Conditions	Yield
Stage #1: 2-chloroethanal; 5-bromo-2-pyridylamine In ethanol; water for 3h; Reflux; Stage #2: With sodium hydrogencarbonate In water	100%
In ethanol; water at 80℃; for 15h;	100%
In ethanol for 6h; Reflux;	98%

5-bromo-2-pyridylamine (1072-97-5) + Bromoacetaldehyde diethyl acetal (2032-35-1) → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Conditions	Yield
With hydrogen bromide In ethanol; water at 103℃;	97%
With hydrogen bromide In ethanol; water at 100℃; for 8h;	87%
With hydrogen bromide In ethanol; water at 100℃; for 8h;	83%
With hydrogenchloride; sodium hydrogencarbonate 1) H2O, a) r.t., b) 80 deg C, 2) r.t.; Yield given. Multistep reaction;

5-bromo-2-pyridylamine (1072-97-5) + bromoacetaldehyde diethyl acetal → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Conditions	Yield
With hydrogen bromide In ethanol; water at 100℃; for 8h;	87.2%

5-bromo-2-pyridylamine (1072-97-5) + chloroacetaldehyde dimethyl acetal (97-97-2) → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Conditions	Yield
Stage #1: 5-bromo-2-pyridylamine; chloroacetaldehyde dimethyl acetal With hydrogenchloride; sodium acetate In ethanol; water for 2.5h; Reflux; Stage #2: With sodium hydrogencarbonate In water pH=Ca. 7;	64.28%
With hydrogenchloride; sodium hydroxide; sodium acetate In water; water ethanol
With hydrogenchloride; sodium hydroxide; sodium acetate In water; water ethanol
With hydrogenchloride; sodium hydroxide; sodium acetate; sodium In water; water ethanol

2-chloroethanal (107-20-0) + 6-bromopyridine-3-amine (13534-97-9) → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Conditions	Yield
In ethanol; water for 18h; Heating / reflux;

5-bromo-2-pyridylamine (1072-97-5) + chloroacetaldehyde diethyl acetal (621-62-5) → 6-bromoimidazo[1,2-a]pyridine (6188-23-4)

Conditions	Yield
Stage #1: chloroacetaldehyde diethyl acetal With hydrogenchloride In water at 90℃; for 0.166667h; Stage #2: 5-bromo-2-pyridylamine With sodium acetate In ethanol; water for 0.333333h; Reflux;

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + methylamine (74-89-5) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → N-methylimidazo[1,2-a]pyridine-6-carboxamide

Conditions	Yield
With palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In tetrahydrofuran; 1,4-dioxane at 85℃; Inert atmosphere; Sealed tube;	100%

phosphonic acid diethyl ester (762-04-9) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → diethyl imidazo[1,2-a]pyridin-6-ylphosphonate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 110℃; for 2h; Inert atmosphere;	100%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-bromo-3-nitro-imidazo[1,2-a]pyridine (64064-71-7)

Conditions	Yield
With sulfuric acid; nitric acid In water at 20℃; for 0.25h;	99%
With nitric acid In sulfuric acid
With nitric acid In sulfuric acid
With nitric acid In sulfuric acid

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + N,N-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → C15H15N3

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2',4',6'-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane In 1,4-dioxane; water at 100℃;	99%

ethyl (3-methylphenyl)phosphinate (1096142-78-7) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → ethyl imidazo[1,2-a]pyridin-6-yl(m-tolyl)phosphinate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 110℃; for 2h; Inert atmosphere;	99%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-bromoimidazo[1,2-a]pyridine-3-sulfonic acid

Conditions	Yield
With chlorosulfonic acid In chloroform for 24h; Reflux;	98%
With chlorosulfonic acid In chloroform for 16h; Reflux;	85%
With chlorosulfonic acid In chloroform for 24h; Reflux;

6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-bromo-3-iodoimidazo[1,2-a]pyridine (474706-74-6)

Conditions	Yield
With N-iodo-succinimide In acetonitrile at 20℃; for 1h;	96%
With N-iodo-succinimide In acetonitrile at 20℃; for 12h; Inert atmosphere;	85%
With N-iodo-succinimide In acetonitrile for 16.0833h;	77%

dimethyl amine (124-40-3) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) + molybdenum hexacarbonyl (13939-06-5, 199620-15-0) → N,N-dimethylimidazo[1,2-a]pyridine-6-carboxamide

Conditions	Yield
With palladium [2'-(amino-κN)[1,1'-biphenyl]-2-yl-κC][[5-(diphenylphosphino)-9,9-dimethyl-9H-xanthen-4-yl]diphenylphosphine-κP](methanesulfonato-κO); 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In tetrahydrofuran; 1,4-dioxane at 85℃; Inert atmosphere; Sealed tube;	96%

N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide (1083326-73-1) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 2,4-difluoro-N-(5-(imidazo[1,2-a]pyridin-6-yl)-2-methoxypyridin-3-yl)benzenesulfonamide (1609565-45-8)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 110℃; for 3h; Suzuki Coupling; Inert atmosphere;	95%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 110℃; for 3h; Suzuki Coupling; Inert atmosphere;	95%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 70℃; for 6h; Inert atmosphere;

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + (2-methylpyridin-3-yl)boronic acid (899436-71-6) → 6-(2-methylpyridin-3-yl)imidazo[1,2-a]pyridine (1611001-25-2)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	95%

diisopropyl hydrogenphosphonate (1809-20-7) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → diisopropyl imidazo[1,2-a]pyridin-6-ylphosphonate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 110℃; for 2h; Inert atmosphere;	94%

ethyl [3-(trifluoromethyl)phenyl]phosphinate (1335150-96-3) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → ethyl imidazo[1,2-a]pyridin-6-yl(3-(trifluoromethyl)phenyl)phosphinate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 110℃; for 4h; Inert atmosphere;	93%

5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (947249-01-6) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 5-(imidazo[1,2-a]pyridin-6-yl)-3-(trifluoromethyl)pyridin-2-amine (1611001-27-4)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	92.12%

2-((difluoromethyl)thio)isoindoline-1,3-dione + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-bromo-3-((difluoromethyl)thio)imidazo[1,2-a]pyridine

Conditions	Yield
With sodium chloride In N,N-dimethyl-formamide at 80℃; for 16h; Schlenk technique; Inert atmosphere;	92%

isobutyraldehyde (78-84-2) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-bromo-3-(2-methyl-propenyl)-imidazo[1,2-a]pyridine

Conditions	Yield
With acetic acid at 130℃; for 10h;	91%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + Diphenylphosphine oxide (4559-70-0) → imidazo[1,2-a]pyridin-6-yldiphenylphosphine oxide

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 110℃; for 5h; Inert atmosphere;	91%

benzaldehyde (100-52-7) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → C21H14Br2N4

Conditions	Yield
With sodium acetate; acetic acid for 24h; Heating;	90%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + pyrimidine 5-boronic acid (109299-78-7) → 6-(pyrimidin-5-yl)imidazo[1,2-a]pyridine (1611001-15-0)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	90%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + cyclopropylboronic acid (411235-57-9) → 6-cyclopropylimidazo[1,2-a]pyridine

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 100℃;	90%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + (6-methylpyridin-3-yl)boronic acid (659742-21-9) → 6-(6-methylpyridin-3-yl)imidazo[1,2-a]pyridine (1611000-95-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	89%

2-methyl-3-buten-2-ol (115-18-4) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → (E)-4-(imidazo[1,2-a]pyridin-6-yl)-2-methylbut-3-en-2-ol

Conditions	Yield
With dicyclohexyl(2',4',6'-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane; palladium diacetate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; for 8h; Sealed tube; Inert atmosphere; Glovebox; Schlenk technique;	89%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + 1-dodecylthiol (112-55-0) → C19H29BrN2S

Conditions	Yield
With copper(l) iodide; oxygen In dimethyl sulfoxide at 100℃; regioselective reaction;	89%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine (1205744-45-1)

Conditions	Yield
With sodium carbonate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In water; N,N-dimethyl-formamide at 130℃; for 0.5h; Microwave irradiation; Inert atmosphere;	89%

4-pyridylboronic acid (1692-15-5) + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-(4-pyridinyl)imidazo[1,2-a]pyridine

Conditions	Yield
With sodium carbonate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine In water; N,N-dimethyl-formamide at 130℃; for 0.5h; Microwave irradiation; Inert atmosphere;	89%

lithium 2,4-dimethoxypyrimidine-5-sulfinate + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-(2,4-dimethoxypyrimidin-5-yl)imidazo[1,2-a]pyridine

Conditions	Yield
Stage #1: lithium 2,4-dimethoxypyrimidine-5-sulfinate With potassium carbonate In 1,4-dioxane for 0.25h; Sealed tube; Inert atmosphere; Stage #2: 6-bromoimidazo[1,2-a]pyridine With palladium diacetate; tricyclohexylphosphine In 1,4-dioxane at 140℃; for 24h; Sealed tube; Inert atmosphere; Sonication;	89%

N-(benzenesulfonyl)-N-[(trifluoromethyl)sulfanyl]benzenesulfonamide + 6-bromoimidazo[1,2-a]pyridine (6188-23-4) → 6-bromo-3-(trifluoromethylthio)imidazo[1,2-a]pyridine

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 1h; Schlenk technique; Inert atmosphere;	88%

6-bromoimidazo[1,2-a]pyridine (6188-23-4) + 2-methoxy-pyridine-5-boronic acid (163105-89-3) → 6-(6-methoxypyridin-3-yl)imidazo[1,2-a]pyridine (1611001-50-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; Inert atmosphere;	87.71%

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 2032-35-1 Bromoacetaldehyde diethyl acetal 
• 107-20-0 2-chloroethanal 
• 97-97-2 chloroacetaldehyde dimethyl acetal 
• 13534-97-9 6-bromopyridine-3-amine 
• 621-62-5 chloroacetaldehyde diethyl acetal 

Downstream Products

• 954373-61-6 6-(4-(methylsulfanyl)phenyl)-imidazo[1,2-a]pyridine 
• 116355-16-9 6-imidazo<1,2-a>pyridinecarboxaldehyde 
• 1065074-14-7 3-bromo-6-bromo-imidazo[1,2-a]pyridine 
• 1202701-37-8 (S)-(N-3-(3-fluoro-4-(imidazo[1,2-a]pyridin-6-yl)phenyl)-2-oxo-5-oxazolidinyl)methylacetamide 
• 1426845-61-5 2-(4-fluorophenyl)-5-(imidazo[1,2-a]pyridin-6-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 1426845-60-4 5-(3-bromo-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 1426845-31-9 2-(4-fluorophenyl)-5-(3-(4-fluorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide 
• 119615-63-3 1,2-dihydro-6-methyl-2-oxo-5-(imidazo[1,2-a]pyridin-6-yl)-3-pyridine carbonitrile hydrochloride 

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