1060812-84-1

Basic information

• Product Name: 5-broMopyrazolo[1,5-a]pyridine
• Synonyms: 5-broMopyrazolo[1,5-a]pyridine;Pyrazolo[1,5-a]pyridine, 5-bromo-
• CAS NO: 1060812-84-1
• Molecular Formula: C₇H₅BrN₂
• Molecular Weight: 197.032
• Mol File: 1060812-84-1.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.69±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 2.00±0.30(Predicted)
• CAS DataBase Reference: 5-broMopyrazolo[1,5-a]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-broMopyrazolo[1,5-a]pyridine(1060812-84-1)
• EPA Substance Registry System: 5-broMopyrazolo[1,5-a]pyridine(1060812-84-1)

Safety Data

• Hazardous Substances Data: 1060812-84-1(Hazardous Substances Data)

Usage

General Description

5-Bromopyrazolo[1,5-a]pyridine is a chemical compound with the molecular formula C7H4BrN3. It is a pyridine derivative that contains a bromine atom and a pyrazole ring. 5-Bromopyrazolo[1,5-a]pyridine has been studied for its potential use in various applications, including as a building block in organic synthesis for the production of pharmaceuticals and agrochemicals. It has also been investigated for its potential biological activities, such as its inhibitory effects on certain enzymes. Additionally, 5-Bromopyrazolo[1,5-a]pyridine has been explored for its use in the development of new materials and functional molecules. Due to its unique structure and potential utility, this compound continues to be of interest to researchers in the chemical and pharmaceutical industries.

Synthetic route

ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate (885276-93-7) → 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1)

Conditions	Yield
With sulfuric acid at 100℃; for 4h;	99.5%
Stage #1: ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate With sulfuric acid; water for 18h; Reflux; Stage #2: With sodium hydroxide In water pH=7;	96%
With sulfuric acid In water at 110℃; for 16h;	60%

5-((tert-butoxycarbonyl)amino)pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester (1101120-33-5) → 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dichloromethane / 18 h / 20 °C 2.1: hydrogen bromide; sodium nitrite / water / 0.25 h / 0 °C 2.2: 0.25 h / 50 °C 2.3: pH 5 3.1: sulfuric acid; water / 18 h / Reflux 3.2: pH 7 View Scheme

ethyl 5-aminopyrazolo[1,5-a]pyridine-3-carboxylate trifluoroacetate → 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen bromide; sodium nitrite / water / 0.25 h / 0 °C 1.2: 0.25 h / 50 °C 1.3: pH 5 2.1: sulfuric acid; water / 18 h / Reflux 2.2: pH 7 View Scheme

N-(4-pyridyl) t-butyl carbamate (98400-69-2) → 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: O-(2,4-dinitrophenyl)hydroxylamine / acetonitrile / 18 h / 40 °C 1.2: 18 h / 20 °C 2.1: dichloromethane / 18 h / 20 °C 3.1: hydrogen bromide; sodium nitrite / water / 0.25 h / 0 °C 3.2: 0.25 h / 50 °C 3.3: pH 5 4.1: sulfuric acid; water / 18 h / Reflux 4.2: pH 7 View Scheme

1-amino-4-bromopyridin-1-ium iodide (1533440-88-8) → 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h 2: sulfuric acid / 80 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: sulfuric acid / 80 °C View Scheme

4-bromopyridin (1120-87-2) → 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: mesitylenesulfonylhydroxylamine / N,N-dimethyl-formamide / 16 h / 0 - 40 °C 1.2: 6 h / 0 - 20 °C 2.1: sulfuric acid / water / 16 h / 110 °C View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + Vilsmeier reagent (3724-43-4, 149409-22-3) → 5-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde (1101120-53-9)

Conditions	Yield
In dichloromethane at 44℃;	100%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → 5-bromo-3-iodopyrazolo[1,5-a]pyridine (1352881-82-3)

Conditions	Yield
With N-iodo-succinimide In methanol at -10 - 20℃; for 18.5h;	97.5%
With N-iodo-succinimide In acetonitrile at 20℃; for 16h;	96%
With N-iodo-succinimide In acetonitrile at 20℃; for 1h;	89%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 5-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde (1101120-53-9)

Conditions	Yield
Stage #1: 5-bromopyrazolo[1,5-a]pyridine; N,N-dimethyl-formamide With trichlorophosphate at 20℃; for 2h; Vilsmeier formylation; Inert atmosphere; Stage #2: With sodium hydroxide In water pH=10;	96%

2-methoxy-4-trifluoromethoxybenzeneboronic acid (355836-10-1) + 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → 5-[2-methoxy-4-(trifluoromethoxy)phenyl]pyrazolo[1,5-a]pyridine

Conditions	Yield
With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium In 1,4-dioxane; water at 80℃; for 16h;	85%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + 3-(methanesulfonyl)phenylboronic acid (373384-18-0) → 5-(3-(methylsulfonyl)phenyl)pyrazolo[1,5-a]pyridine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 12h; Suzuki Coupling; Inert atmosphere;	77%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarbonitrile (1206641-31-7) → 1-(4-pyrazolo[1,5-a]pyridin-5-ylphenyl)cyclopropanecarbonitrile

Conditions	Yield
With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium In 1,4-dioxane; water at 80℃; for 16h;	76%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + 3-(cyclopropylsulfonyl)phenylboronic acid (1020204-12-9) → 5-(3-(cyclopropylsulfonyl)phenyl)pyrazolo[1,5-a]pyridine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water; N,N-dimethyl-formamide at 90℃; for 12h; Suzuki Coupling; Inert atmosphere;	75%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + bis(pinacol)diborane (73183-34-3) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 8h; Inert atmosphere;	75%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 105 - 110℃; for 1.5h;

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide (1083326-73-1) → 2,4-difluoro-N-(2-methoxy-5-(pyrazolo[1,5-a]pyridin-5-yl)pyridin-3-yl)benzenesulfonamide (1621718-79-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere;	73%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + Cyclopropylamine (765-30-0) → N-cyclopropylpyrazolo[1,5-a]pyridin-5-amine (1610612-76-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 90℃; for 2h; Inert atmosphere; Microwave irradiation;	62%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + 2-[4-(1-methoxy-1-methyl-ethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 5-[4-(1-methoxy-1-methyl-ethyl)phenyl]pyrazolo[1,5-a]pyridine

Conditions	Yield
With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium In 1,4-dioxane; water at 80℃; for 16h;	59%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine → 5-[6-(2,2,2-trifluoroethoxy)-3-pyridyl]pyrazolo[1,5-a]pyridine

Conditions	Yield
With potassium phosphate; bis[tris( 1,1-dimethylethyl)phosphine]-palladium In 1,4-dioxane; water at 80℃; for 16h;	53%

t-butyl bromide (507-19-7) + 5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → 5-bromo-3-tert-butylpyrazolo[1,5-a]pyridine

Conditions	Yield
Stage #1: t-butyl bromide With aluminum (III) chloride In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 5-bromopyrazolo[1,5-a]pyridine In dichloromethane at 0℃; for 3h; Inert atmosphere;	46%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) + 2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidine → 2-(6-methylpyridin-2-yl)-3-(pyrazolo[1,5-a]pyridine-5-yl)imidazo[1,2-a]pyrimidine

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine In 1,4-dioxane at 120℃;	38%

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → C13H14N2OSi

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → C9H9BrN4

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: sodium hydrogencarbonate / methanol View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → C12H14N4

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / Inert atmosphere; Reflux 3.1: sodium hydrogencarbonate / methanol View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → C11H12N4

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Inert atmosphere; Reflux 3.1: sodium hydrogencarbonate / methanol View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → C11H10N4

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 3.1: methanol; potassium carbonate / 2 h 4.1: sodium hydrogencarbonate / methanol View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → 5-cyclopropylpyrazolo[1,5-a]pyridine-3-carbaldehyde (1101120-63-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / Inert atmosphere; Reflux View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → 5-vinylpyrazolo[1,5-a]pyridine-3-carbaldehyde (1101120-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Inert atmosphere; Reflux View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → 5-ethynylpyrazolo[1,5-a]pyridine-3-carbaldehyde (1101120-65-3)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 3.1: methanol; potassium carbonate / 2 h View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → N'-((5-bromopyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide (1101118-18-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: sodium hydrogencarbonate / methanol 3.1: sodium hydrogencarbonate / methanol / 0.5 h View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → N'-((5-cyclopropylpyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide (1101118-21-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 18 h / Inert atmosphere; Reflux 3.1: sodium hydrogencarbonate / methanol 4.1: sodium hydrogencarbonate / methanol / 0.5 h View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → N,2-dimethyl-5-nitro-N'-((5-vinylpyrazolo[1,5-a]pyridin-3-yl)methylene)benzenesulfonohydrazide (1101118-20-0)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 2 h / Inert atmosphere; Reflux 3.1: sodium hydrogencarbonate / methanol 4.1: sodium hydrogencarbonate / methanol / 0.5 h View Scheme

5-bromopyrazolo[1,5-a]pyridine (1060812-84-1) → N'-((5-ethynylpyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide (1101118-22-2)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: trichlorophosphate / 2 h / 20 °C / Inert atmosphere 1.2: pH 10 2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere 3.1: methanol; potassium carbonate / 2 h 4.1: sodium hydrogencarbonate / methanol 5.1: sodium hydrogencarbonate / methanol / 0.5 h View Scheme

Upstream product

• 1101120-33-5 5-[(tert-butoxycarbonyl)amino]pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester 
• 1533440-88-8 1-amino-4-bromopyridin-1-ium iodide 
• 1120-87-2 4-bromopyridin 
• 98400-69-2 N-(4-pyridyl) t-butyl carbamate 
• 885276-93-7 ethyl 5-bromopyrazolo[1,5-a]pyridine-3-carboxylate 

Downstream Products

• 1101118-18-6 N'-((5-bromopyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide 
• 1101118-21-1 N'-((5-cyclopropylpyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide 
• 1101118-20-0 N,2-dimethyl-5-nitro-N'-((5-vinylpyrazolo[1,5-a]pyridin-3-yl)methylene)benzenesulfonohydrazide 
• 1101118-22-2 N'-((5-ethynylpyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethyl-5-nitrobenzenesulfonohydrazide 
• 1101120-53-9 5-bromopyrazolo[1,5-a]pyridine-3-carbaldehyde 
• 1352881-82-3 5-bromo-3-iodopyrazolo[1,5-a]pyridine 
• 1610611-09-0 5-cyano-N-methyl-N-(3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridin-5-yl)picolinamide 
• 1621718-79-3 2,4-difluoro-N-(2-methoxy-5-(pyrazolo[1,5-a]pyridin-5-yl)pyridin-3-yl)benzenesulfonamide 
• 1621718-41-9 N-(2-chloro-5-(3-cyanopyrazolo[1,5-a]pyridin-5-yl)pyridin-3-yl)-2,4-difluorobenzenesulfonamide 
• 1352900-95-8 5-bromopyrazolo[1,5-a]pyridine-3-carbonitrile 
• 1621718-37-3 N-(5-(3-cyanopyrazole[1,5-a]pyridin-5-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzene sulfonamide 
• 1621718-60-2 2,4-difluoro-N-(5-(3-(3-hydroxyprop-1-yn-1-yl)pyrazolo[1,5-a]pyridin-5-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 
• 1621718-80-6 2,4-difluoro-N-(5-(3-iodopyrazolo[1,5-a]pyridin-5-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 
• 1621718-62-4 2,4-difluoro-N-(5-(3-(3-hydroxy-3-methylbut-1-yn-1-yl)pyrazolo[1,5-a]pyridin-5-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 

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