5-Bromo-1H-pyrazolo[3,4-b]pyridine supplier

Name
5-BROMO-1H-PYRAZO[3,4-B]PYRIDINE
EINECS -0
CAS No. 875781-17-2
Article Data16
CAS DataBase
Density 1.895 g/cm³
Solubility
Melting Point 198.0 to 202.0 °C
Formula C₆H₄BrN₃
Boiling Point 329 °C at 760 mmHg
Molecular Weight 198.022
Flash Point 152.8 °C
Transport Information
Appearance
Safety 24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 5-Bromo-1-hydropyrazolo[3,4-b]pyridine;
PSA 41.57000
LogP 1.72040

Synthetic route

: 875781-15-0
5-bromo-2-fluoro-pyridine-3-carbaldehyde

: 875781-17-2
5-bromo-7-azaindazole

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

Conditions

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%

: 2065-75-0
2-Bromo-malonaldehyde

: 1225387-53-0
3(5)-aminopyrazole

: 875781-17-2
5-bromo-7-azaindazole

Conditions

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

: 2065-75-0
2-Bromo-malonaldehyde

: 1225387-53-0
3(5)-aminopyrazole

A: 705263-10-1
6-bromo-pyrazolo[1,5-α]pyrimidine

B: 875781-17-2
5-bromo-7-azaindazole

Conditions

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

...Expand

: 1820-80-0
3-aminopyrazole

: 2065-75-0
2-Bromo-malonaldehyde

: 875781-17-2
5-bromo-7-azaindazole

Conditions

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

: 875781-16-1
C8H10BrN3O2*ClH

: 875781-17-2
5-bromo-7-azaindazole

Conditions

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;

: 1083326-08-2
5-bromo-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-2(1H)-pyridinone hydrazone

: 875781-17-2
5-bromo-7-azaindazole

Conditions

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

: 766-11-0
5-bromo-2-fluoropyridine

: 875781-17-2
5-bromo-7-azaindazole

Conditions

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

: 110-87-2
3,4-dihydro-2H-pyran

: 875781-17-2
5-bromo-7-azaindazole

: 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

Conditions

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%

: 875781-17-2
5-bromo-7-azaindazole

: 875781-18-3
5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine

Conditions

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%

: 875781-17-2
5-bromo-7-azaindazole

: 24424-99-5
di-tert-butyl dicarbonate

: tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Conditions

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%

: 875781-17-2
5-bromo-7-azaindazole

: 100-97-0
hexamethylenetetramine

: 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 5-bromo-1H-pyrazolo[3,4-b]pyridine 7-oxide

Conditions

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;

: 557-21-1
zinc(II) cyanide

: 875781-17-2
5-bromo-7-azaindazole

: 1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 723281-55-8
[3-(morpholin-4-ylcarbonyl)phenyl]boronic acid

A: 875781-22-9
morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone

B: 791-28-6
Triphenylphosphine oxide

Conditions

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

...Expand

: 875781-17-2
5-bromo-7-azaindazole

: 824-94-2
p-methoxybenzyl chloride

: 1111638-35-7
5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine

Conditions

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%

: 875781-17-2
5-bromo-7-azaindazole

: 1066-54-2
trimethylsilylacetylene

: 1207351-08-3
5-((trimethylsilyl) ethynyl)-1H-pyrazolo[3,4-b]pyridine

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 1186608-66-1
5-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazolo[3,4-b]pyridine

Conditions

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;

: 875781-17-2
5-bromo-7-azaindazole

: 74-88-4
methyl iodide

: 887115-56-2
5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine

Conditions

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%

: 875781-17-2
5-bromo-7-azaindazole

: 1312942-04-3
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

: 1312939-70-0
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

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 74-88-4
methyl iodide

A: 887115-56-2
5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine

B: 5-bromo-2-methyl-2H-pyrazolo[3,4-b]pyridine

Conditions

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%

...Expand

: 875781-17-2
5-bromo-7-azaindazole

: 86864-60-0
2-(tert-butyldimethylsilyloxy)ethyl bromide

: 5-bromo-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazolo[3,4-b]pyridine

Conditions

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

: 516-12-1
N-iodo-succinimide

: 875781-17-2
5-bromo-7-azaindazole

: 875781-18-3
5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 99769-19-4
[3-(methoxycarbonyl)phenyl]boronic acid

: 875781-27-4
methyl 3-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 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

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%

: 875781-17-2
5-bromo-7-azaindazole

: 2,4-difluoro-3-ethynylaniline

: 3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-2,4-difluoroaniline

Conditions

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

: 705262-42-6
(2-(6-methylpyridin-2-yl)-5,6-dihydro-4Hpyrrolo[1,2-b]pyrazol-3-yl)boronic acid

: 875781-17-2
5-bromo-7-azaindazole

: 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

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

: 875781-17-2
5-bromo-7-azaindazole

: 832114-00-8
3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole

: 3,5-dimethyl-4-(1H-pyrazolo[3,4-b]pyridin-5-yl)isoxazole

Conditions

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

: 67-56-1
methanol

: 875781-17-2
5-bromo-7-azaindazole

: 201230-82-2
carbon monoxide

: 1196156-42-9
1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester

Conditions

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;

...Expand

: 875781-17-2
5-bromo-7-azaindazole

: 35634-10-7
[1.1.1]propellane

: C21H29IO6

: C16H18BrN3O

Conditions

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%

...Expand

: 875781-17-2
5-bromo-7-azaindazole

: 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

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

: 875781-17-2
5-bromo-7-azaindazole

: 1552300-42-1
7-amino-3-bromo-1-cyclopentyl-5-methyl-1,6-naphthyridin-2(1H)-one

: 1552300-56-7
7-amino-1-cyclopentyl-5-methyl-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1,6-naphthyridin-2(1H)-one

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 2-(4-(1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)acetic acid

Conditions

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

: 875781-17-2
5-bromo-7-azaindazole

: 1083325-84-1
2-(4-morpholinyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline

: 1083320-98-2
2-(4-morpholinyl)-7-(1H-pyrazolo[3,4-b]pyridin-5-yl)quinoxaline

Conditions

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

5-Bromo-1H-pyrazolo[3,4-b]pyridine Chemical Properties

Molecule structure of 5-Bromo-1H-pyrazolo[3,4-b]pyridine (CAS NO.875781-17-2):

Molecular Weight: 198.0201 g/mol
Molecular Formula: C₆H₄BrN₃
Density: 1.894 g/cm³
Boiling Point: 329 °C at 760 mmHg
Flash Point: 152.8 °C
Index of Refraction: 1.745
Molar Refractivity: 42.4 cm³
Molar Volume: 104.5 cm³
Polarizability: 16.8×10^-24 cm³
Surface Tension: 76.9 dyne/cm
Enthalpy of Vaporization: 54.88 kJ/mol
Vapour Pressure: 0.00035 mmHg at 25 °C
InChI: InChI=1/C6H4BrN3/c7-5-1-4-2-9-10-6(4)8-3-5/h1-3H,(H,8,9,10) Copy
InChIKey: BASYLPMLKGQZOG-UHFFFAOYAK
Product Categories of 5-Bromo-1H-pyrazolo[3,4-b]pyridine (CAS NO.875781-17-2): CHIRAL CHEMICALS; Building Blocks; Pyrazolo[x,x-y]pyridine

5-Bromo-1H-pyrazolo[3,4-b]pyridine Specification

5-Bromo-1H-pyrazolo[3,4-b]pyridine (CAS NO.875781-17-2) is also named as 1H-pyrazolo[3,4-b]pyridine, 5-bromo- .

Product Name

5-BROMO-1H-PYRAZO[3,4-B]PYRIDINE

Synthetic route

5-Bromo-1H-pyrazolo[3,4-b]pyridine Chemical Properties

5-Bromo-1H-pyrazolo[3,4-b]pyridine Specification

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