875781-17-2

Basic information

• Product Name: 5-BROMO-1H-PYRAZO[3,4-B]PYRIDINE
• Synonyms: 5-bromo-1H-pyrazoio[3,4-b]pyridine;5-Bromopyrazolo[3,4-b]pyridine;5-Bromo-1H-pyrazolo[3,4-b]pyridine;4-b]pyridine;5-broMo-1H-pyrazolo[3;1H-Pyrazolo[3,4-b]pyridine, 5-broMo-;7-Aza-5-bromo-1H-indole;5-Bromopyrazolo[3,4-b]pyridine
• CAS NO: 875781-17-2
• Molecular Formula: C₆H₄BrN₃
• Molecular Weight: 198.023
• EINECS: -0
• Product Categories: CHIRAL CHEMICALS;Building Blocks;Pyrazolo[x,x-y]pyridine
• Mol File: 875781-17-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 198.0 to 202.0 °C
• Boiling Point: 329 °C at 760 mmHg
• Flash Point: 152.8 °C
• Appearance: /Solid
• Density: 1.895 g/cm³
• Vapor Pressure: 0.00148mmHg at 25°C
• Refractive Index: 1.68
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.66±0.40(Predicted)
• CAS DataBase Reference: 5-BROMO-1H-PYRAZO[3,4-B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-1H-PYRAZO[3,4-B]PYRIDINE(875781-17-2)
• EPA Substance Registry System: 5-BROMO-1H-PYRAZO[3,4-B]PYRIDINE(875781-17-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 875781-17-2(Hazardous Substances Data)

Usage

Uses

5-Bromo-1H-pyrazolo[3,4-b]pyridine is a pyridine (P998910) derivative and useful building block, seen in its use in the synthetic preparation of 7-?azaindazole chalcone derivatives as analgesics and anti-?inflammatories.

InChI:InChI=1/C7H7N3/c1-5-2-6-4-9-10-7(6)8-3-5/h2-4H,1H3,(H,8,9,10)

Synthetic route

5-bromo-2-fluoro-pyridine-3-carbaldehyde (875781-15-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
With hydrazine hydrate In water at 65℃; for 15h; Inert atmosphere;	82%
With hydrazine In ethanol Heating / reflux;	46%
With hydrazine hydrate In ethanol at 100℃; for 8h;	40%

C12H18BrN3O2*ClH → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
Stage #1: C12H18BrN3O2*ClH With hydrogenchloride In ethanol; water at 20 - 65℃; for 16h; Stage #2: With sodium carbonate In ethanol; water	50%

2-Bromo-malonaldehyde (2065-75-0) + 3(5)-aminopyrazole (1225387-53-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
In acetic acid for 6h; Heating; Reflux; Inert atmosphere of N2;	25%

2-Bromo-malonaldehyde (2065-75-0) + 3(5)-aminopyrazole (1225387-53-0) → 6-bromo-pyrazolo[1,5-α]pyrimidine (705263-10-1) + 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
In ethanol at 20℃; Heating / reflux;	A 13.8% B 2.1%

3-aminopyrazole (1820-80-0) + 2-Bromo-malonaldehyde (2065-75-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
With acetic acid for 2h; Heating / reflux;	11%

C8H10BrN3O2*ClH (875781-16-1) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
Stage #1: C8H10BrN3O2*ClH With hydrogenchloride In ethanol; water at 20 - 65℃; for 16h; Stage #2: With sodium hydrogencarbonate In ethanol; water pH=8;

5-bromo-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-2(1H)-pyridinone hydrazone (1083326-08-2) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
With hydrogenchloride; water In ethanol at 20 - 60℃;

5-bromo-2-fluoropyridine (766-11-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.17 h / -78 °C 2.1: hydrazine hydrate / ethanol / 8 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 3 h / -65 - -30 °C / Inert atmosphere 1.2: 0.08 h 2.1: hydrazine hydrate / tetrahydrofuran; ethanol; water / 1 h / 45 - 80 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -90 - -85 °C 1.2: 0.5 h / -80 °C 2.1: hydrazine hydrate / ethanol / 12 h / 75 - 80 °C View Scheme

3,4-dihydro-2H-pyran (110-87-2) + 5-bromo-7-azaindazole (875781-17-2) → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane; acetonitrile at 20℃; for 24h;	100%
With toluene-4-sulfonic acid In toluene at 100℃; for 4h;	98%
With toluene-4-sulfonic acid at 25 - 30℃; for 3h;	60.7%

5-bromo-7-azaindazole (875781-17-2) → 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine (875781-18-3)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With iodine; potassium hydroxide In N,N-dimethyl-formamide for 3.5h; Stage #2: With iodine; sodium hydroxide In 1,4-dioxane at 40℃; for 23h;	97%
Stage #1: 5-bromo-7-azaindazole With potassium hydroxide In N,N-dimethyl-formamide for 0.166667h; Stage #2: With iodine In N,N-dimethyl-formamide at 20℃; for 3.5h;	96%
Stage #1: 5-bromo-7-azaindazole With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With iodine In N,N-dimethyl-formamide at 45℃; for 1h;	92%

5-bromo-7-azaindazole (875781-17-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Conditions	Yield
With dmap; triethylamine In acetonitrile at 20℃; for 3.25h; Inert atmosphere;	93%
With dmap; triethylamine In dichloromethane at 20℃; for 24h;	85%
With dmap In tetrahydrofuran for 14h; Reflux;	68%

5-bromo-7-azaindazole (875781-17-2) + hexamethylenetetramine (100-97-0) → 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde

Conditions	Yield
With acetic acid In water for 12h; Sommelet Aldehyde Synthesis; Reflux;	92%

5-bromo-7-azaindazole (875781-17-2) → 5-bromo-1H-pyrazolo[3,4-b]pyridine 7-oxide

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In ethyl acetate at 20 - 50℃; for 5.5h;	91%
With dihydrogen peroxide; trifluoroacetic acid at 60℃; for 12h;

zinc(II) cyanide (557-21-1) + 5-bromo-7-azaindazole (875781-17-2) → 1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1-methyl-pyrrolidin-2-one at 92℃; for 5h; Temperature;	90%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl acetamide; water at 80℃; for 6h; Inert atmosphere;	82%
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In water; N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;	82%
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 85℃; for 10h; Inert atmosphere; Large scale;	535 g

5-bromo-7-azaindazole (875781-17-2) + [3-(morpholin-4-ylcarbonyl)phenyl]boronic acid (723281-55-8) → morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone (875781-22-9) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 175℃; for 1h; Microwave irradiation;	A 80% B 20%

5-bromo-7-azaindazole (875781-17-2) + p-methoxybenzyl chloride (824-94-2) → 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (1111638-35-7)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 0 - 20℃;	77.2%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	68.3%

5-bromo-7-azaindazole (875781-17-2) + trimethylsilylacetylene (1066-54-2) → 5-((trimethylsilyl) ethynyl)-1H-pyrazolo[3,4-b]pyridine (1207351-08-3)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	73.7%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	73.7%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile for 20h; Reflux; Inert atmosphere;	63%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20 - 100℃; for 20h; Sonogashira Cross-Coupling; Inert atmosphere;
With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere;	3.5 g

5-bromo-7-azaindazole (875781-17-2) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 5-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazolo[3,4-b]pyridine (1186608-66-1)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 20℃; for 0.5h;	73%
Stage #1: 5-bromo-7-azaindazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃;	43%
Stage #1: 5-bromo-7-azaindazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.416667h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0℃; for 2h; Stage #3: With ammonium chloride In water; N,N-dimethyl-formamide; mineral oil Cooling;

5-bromo-7-azaindazole (875781-17-2) + methyl iodide (74-88-4) → 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine (887115-56-2)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide at 25℃; Inert atmosphere;	73%

5-bromo-7-azaindazole (875781-17-2) + propane-1-sulfonic acid {2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide (1312942-04-3) → propane-1-sulfonic acid {2,4-difluoro-3-[5-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide (1312939-70-0)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water; acetonitrile at 145℃; for 0.75h; microwave irradiation;	72%

5-bromo-7-azaindazole (875781-17-2) + methyl iodide (74-88-4) → 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine (887115-56-2) + 5-bromo-2-methyl-2H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2h;	A 7% B 69%
With sodium hexamethyldisilazane In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 3h;	A 46% B 3%

5-bromo-7-azaindazole (875781-17-2) + 2-(tert-butyldimethylsilyloxy)ethyl bromide (86864-60-0) → 5-bromo-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 18 - 25℃;	66%

N-iodo-succinimide (516-12-1) + 5-bromo-7-azaindazole (875781-17-2) → 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine (875781-18-3)

Conditions	Yield
In 1,2-dichloro-ethane Reflux;	65.8%

5-bromo-7-azaindazole (875781-17-2) + [3-(methoxycarbonyl)phenyl]boronic acid (99769-19-4) → methyl 3-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate (875781-27-4)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 110℃; for 15h; Microwave irradiation;	65%

5-bromo-7-azaindazole (875781-17-2) + N-(3-ethynyl-2,4-difluborophenyl)pyridine-3-ylsulfonamide → N-(3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-2,4-difluorophenyl)pyridine-3-sulfonamide

Conditions	Yield
With copper(l) iodide; tri-tert-butyl phosphine; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 24h; Sonogashira Cross-Coupling; Sealed tube; Inert atmosphere;	64%

5-bromo-7-azaindazole (875781-17-2) + 2,4-difluoro-3-ethynylaniline → 3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-2,4-difluoroaniline

Conditions	Yield
With copper(l) iodide; tri-tert-butyl phosphine; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 24h; Sonogashira Cross-Coupling; Sealed tube; Inert atmosphere;	63%
With copper(l) iodide; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); triethylamine In dimethyl sulfoxide at 120℃; for 1h; Sonogashira Cross-Coupling; Microwave irradiation;	61%
With copper(l) iodide; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); triethylamine In dimethyl sulfoxide at 120℃; for 1h; Microwave irradiation;	2.15 g

(2-(6-methylpyridin-2-yl)-5,6-dihydro-4Hpyrrolo[1,2-b]pyrazol-3-yl)boronic acid (705262-42-6) + 5-bromo-7-azaindazole (875781-17-2) → 5-[2-[6-methyl-(pyridin-2-yl)]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In water; dimethyl sulfoxide at 110℃; for 0.166667h; Microwave irradiation;	56%

5-bromo-7-azaindazole (875781-17-2) + 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (832114-00-8) → 3,5-dimethyl-4-(1H-pyrazolo[3,4-b]pyridin-5-yl)isoxazole

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In water; acetonitrile at 110℃; for 0.25h; Microwave irradiation;	55%

methanol (67-56-1) + 5-bromo-7-azaindazole (875781-17-2) + carbon monoxide (201230-82-2) → 1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester (1196156-42-9)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; for 12h;	46%
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 12h;

5-bromo-7-azaindazole (875781-17-2) + [1.1.1]propellane (35634-10-7) + C21H29IO6 → C16H18BrN3O

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); copper acetylacetonate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In 1,4-dioxane Irradiation;	46%

5-bromo-7-azaindazole (875781-17-2) + ethyl 1-methyl-7-((trimethylsilyl)ethynyl)-1H-indole-2-carboxylate → ethyl 7-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-1-methyl-1H-indole-2-carboxylate

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine In N,N-dimethyl-formamide Heating;	42%

5-bromo-7-azaindazole (875781-17-2) + 7-amino-3-bromo-1-cyclopentyl-5-methyl-1,6-naphthyridin-2(1H)-one (1552300-42-1) → 7-amino-1-cyclopentyl-5-methyl-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1,6-naphthyridin-2(1H)-one (1552300-56-7)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 7-amino-3-bromo-1-cyclopentyl-5-methyl-1,6-naphthyridin-2(1H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;	28%

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid + 5-bromo-7-azaindazole (875781-17-2) → 2-(4-(1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)acetic acid

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 100℃; for 3h; Inert atmosphere;	28%

5-bromo-7-azaindazole (875781-17-2) + 2-(4-morpholinyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (1083325-84-1) → 2-(4-morpholinyl)-7-(1H-pyrazolo[3,4-b]pyridin-5-yl)quinoxaline (1083320-98-2)

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 110℃; for 18h;	26%

Upstream product

• 1820-80-0 3-aminopyrazole 
• 2065-75-0 2-Bromo-malonaldehyde 
• 766-11-0 5-bromo-2-fluoropyridine 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 875781-15-0 5-bromo-2-fluoro-3-pyridinecarboxaldehyde 
• 1083326-08-2 5-bromo-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-2(1H)-pyridinone hydrazone 
• 875781-16-1 C₈H₁₀BrN₃O₂*ClH 

Downstream Products

• 875781-18-3 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine 
• 1111638-35-7 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine 
• 916326-37-9 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde 
• 887115-56-2 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine 
• 1316852-65-9 5-bromo-2-methyl-2H-pyrazolo[3,4-b]pyridine 
• 893722-46-8 5-bromo-3-chloro-1H-pyrazolo[3,4-b]pyridine 
• 1196156-42-9 1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester 
• 952182-02-4 1H-pyrazolo[3,4-b] pyridine-5-carboxylic acid 
• 1581701-34-9 N-(2-methyl-5-((4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)carbamoyl)phenyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide 
• 1186608-72-9 5-bromo-3-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine 
• 1448705-58-5 C₃₆H₄₃F₃N₆O₂Si 

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