130284-53-6

Basic information

• Product Name: 2-Chloro-3-bromo-5-aminopyridine
• Synonyms: 5-BROMO-6-CHLOROPYRIDIN-3-AMINE;5-AMINO-3-BROMO-2-CHLOROPYRIDINE;2-chloro-3-bromo-5-aminopyridine;5-BROMO-6-CHLORO-3-AMINOPYRIDINE;2-CHLORO-3-BROMO-5-AMINOPYRIDINE 98+%;3-Bromo-2-chloro-5-aminopyridine;2-chloro-3-bromopyridin-5-amine;5-bromo-6-chloropyridin-3-aminr
• CAS NO: 130284-53-6
• Molecular Formula: C₅H₄BrClN₂
• Molecular Weight: 207.46
• Product Categories: Pyridine;Pyridines;Boronic Acid
• Mol File: 130284-53-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 120-122°C
• Boiling Point: 336.729 °C at 760 mmHg
• Flash Point: 157.4 °C
• Appearance: /
• Density: 1.835 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.648
• Storage Temp.: 2-8°C(protect from light)
• PKA: 0.86±0.10(Predicted)
• CAS DataBase Reference: 2-Chloro-3-bromo-5-aminopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-bromo-5-aminopyridine(130284-53-6)
• EPA Substance Registry System: 2-Chloro-3-bromo-5-aminopyridine(130284-53-6)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-41
• Safety Statements: 26-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 130284-53-6(Hazardous Substances Data)

Usage

Description

2-Chloro-3-bromo-5-aminopyridine is an organic chemical compound characterized by a molecular formula C5H4BrClN2. It is a heterocyclic aromatic compound that features a pyridine ring with chlorine, bromine, and amino groups attached to it. 2-Chloro-3-bromo-5-aminopyridine is recognized for its versatility in organic synthesis and its potential as a pharmaceutical intermediate, given its biological activity and ongoing research for its role in the development of new drugs.

Uses

Used in Pharmaceutical Synthesis:
2-Chloro-3-bromo-5-aminopyridine is utilized as a building block in the synthesis of various pharmaceuticals. Its unique structure allows for the introduction of functional groups into organic molecules, making it a valuable component in the creation of new drugs.
Used in Agrochemical Development:
In the agrochemical industry, 2-Chloro-3-bromo-5-aminopyridine serves as a key intermediate in the development of new compounds designed to protect crops and enhance agricultural productivity.
Used in Organic Material Synthesis:
2-Chloro-3-bromo-5-aminopyridine is also employed in the synthesis of organic materials, where its structural properties contribute to the formation of novel materials with specific applications in various industries.
Used in Chemical Reactions as a Reagent:
2-Chloro-3-bromo-5-aminopyridine is used as a reagent in chemical reactions to introduce functional groups into organic molecules, facilitating the creation of a wide range of chemical products.

InChI:InChI=1/C5H4BrClN2/c6-4-1-3(8)2-9-5(4)7/h1-2H,8H2

Synthetic route

3-bromo-2-chloro-5-nitropyridine (5470-17-7) → 2-chloro-3-bromo-5-aminopyridine (130284-53-6)

Conditions	Yield
With hydrogen In tetrahydrofuran at 37℃; under 2250.23 Torr; for 18h; chemoselective reaction;	92%
With iron; acetic acid In water for 2h; below 50 deg C;	87%
With ammonium chloride; zinc In methanol at 90℃; for 2h;	70.6%

3-bromo-2-hydroxy-5-nitropyridine (15862-33-6) → 2-chloro-3-bromo-5-aminopyridine (130284-53-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 94 percent / POCl3, quinoline / 2 h / 120 °C 2: 87 percent / Fe, AcOH / H2O / 2 h / below 50 deg C View Scheme

3,4,5,6-tetrahydro-2H-pyran-4-carbaldehyde (50675-18-8) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloro-N-((tetrahydro-2H-pyran-4-yl)methyl)pyridin-3-amine (1378034-59-3)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 20h;	97%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 3-bromo-2-chloro-5-iodopyridine

Conditions	Yield
Stage #1: 5-amino-3-bromo-2-chloropyridine With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Sandmeyer Reaction; Stage #2: In water at 0 - 20℃; Sandmeyer Reaction;	89%

tri-n-butyl(vinyl)tin (7486-35-3) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 6-chloro-5-vinylpyridin-3-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); lithium chloride In 1,4-dioxane for 24h; Reflux;	89%

4-vinylpyridine (100-43-6) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine (552330-65-1)

Conditions	Yield
With triethylamine; tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 15h;	84%
With tris(dibenzylideneacetone)dipalladium (0); triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 15h;

4-vinylpyridine (100-43-6) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) + tris-(o-tolyl)phosphine (6163-58-2) → 6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine (552330-65-1)

Conditions	Yield
With triethylamine; tris-(dibenzylideneacetone)dipalladium(0) In ethyl acetate; N,N-dimethyl-formamide	84%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + N-tert-butyloxycarbonyl-tryptophanal (82689-14-3) → 1,1-dimethylethyl [(1S)-2-[(5-bromo-6-chloro-3-pyridinyl)amino]-1-(1H-indol-3-ylmethyl)ethyl]carbamate (864773-87-5)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	75%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + Phe-COOH → N-(5-bromo-6-chloro-3-pyridinyl)-N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-phenylalaninamide

Conditions	Yield
Stage #1: Phe-COOH With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 2h; Heating / reflux; Stage #2: 5-amino-3-bromo-2-chloropyridine In tetrahydrofuran for 1h; Heating / reflux;	59.4%

3-phenyl-propionaldehyde (104-53-0) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloro-N-(3-phenylpropyl)-3-pyridinamine (864773-02-4)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 1h;	50%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + acetic anhydride (108-24-7) → N-(5-bromo-6-chloropyridin-3-yl)acetamide

Conditions	Yield
at 20℃; for 1h;	49.5%

2,2-dimethyltetrahydro-2H-pyran-4-carbaldehyde (34941-21-4) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloro-N-((2,2-dimethyltetrahydro-2H-pyran-4-yl)methyl)pyridin-3-amine (1378034-68-4)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 2h;	45.2%

5-methylfuran-2-boronic acid (62306-79-0) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 6-chloro-5-(5-methylfuran-2-yl)pyridin-3-amine

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate In 1-methyl-pyrrolidin-2-one; water at 150℃; for 2h; Inert atmosphere;	22%

2-chloro-3-bromo-5-aminopyridine (130284-53-6) + acetic anhydride (108-24-7) → 5-bromo-6-chloropyridin-3-yl acetate (130284-55-8)

Conditions	Yield
With tetrafluoroboric acid; sodium nitrite 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h; Yield given. Multistep reaction;

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2-chloro-5-iodo-3-[(E)-2-pyridin-4-ylvinyl]pyridine (552330-68-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → (1R)-3-{6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-yl}-1-(1H-indol-3-ylmethyl)propylamine

Conditions	Yield
Multi-step reaction with 4 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h 3.1: 9-BBN / 0 - 20 °C 3.2: 40 percent / PdCl2(dppf); Cs2CO3 / dimethylformamide / 8 h / 50 °C 4.1: TFA / CH2Cl2 / 2 h / 20 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → N1-[6-chloro-5-(2-pyridin-4-yl-vinyl)-pyridin-3-yl]-3-(1H-indol-3-yl)-propane-1,2-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: acetic acid / methanol / 3 h / Heating 2.2: Ti(i-PrO)4; NaBH3CN / methanol / 1 h 3.1: TFA / CH2Cl2 / 2 h / 20 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → tert-butyl (1R)-3-{6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-yl}-1-(1H-indol-3-ylmethyl)propylcarbamate (552330-71-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: NaNO2; aq. H2SO4 / 5 h / 0 °C 2.2: 70 percent / NaI / 2 h 3.1: 9-BBN / 0 - 20 °C 3.2: 40 percent / PdCl2(dppf); Cs2CO3 / dimethylformamide / 8 h / 50 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → [1-{[6-chloro-5-(2-pyridin-4-yl-vinyl)-pyridin-3-ylamino]-methyl}-2-(1H-indol-3-yl)-ethyl]-carbamic acid tert-butyl ester (882170-52-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Pd2(dba)3; P(o-Tol)3; Et3N / dimethylformamide / 15 h / 100 °C 2.1: acetic acid / methanol / 3 h / Heating 2.2: Ti(i-PrO)4; NaBH3CN / methanol / 1 h View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 5-bromo-6-chloropyridin-3-ol (130115-85-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) HBF4, NaNO2 / 1)water, 0 deg C, 1 h, 2) 70 deg C, 1 h 2: 98 percent / 2 N KOH / 0.5 h / 5 °C View Scheme
Stage #1: 5-amino-3-bromo-2-chloropyridine With sulfuric acid; sodium nitrite In water at 0 - 25℃; for 0.5h; Stage #2: With acetic acid In water at 100℃; for 12h;

1-azaadamantane-4-one (42949-24-6) + 2-chloro-3-bromo-5-aminopyridine (130284-53-6) + toluene-4-sulfonic acid (104-15-4) → (4s)-N-(5-bromo-6-chloropyridin-3-yl)-1-azatricyclo[3.3.1.13,7]decan-4-amine 4-methylbenzenesulfonate

Conditions	Yield
Stage #1: 1-azaadamantane-4-one; 5-amino-3-bromo-2-chloropyridine With magnesium sulfate; acetic acid for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 14h; Stage #3: toluene-4-sulfonic acid In ethanol; ethyl acetate at -10 - 20℃; Heating / reflux;

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → (6-chloro-pyridin-3-yl)-(tetrahydro-pyran-4-ylmethyl)-amine (1378034-61-7) + 2,5'-dichloro-2'-fluoro-N-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridin-5-amine (1378034-60-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → N2'-(trans-4-aminocyclohexyl)-2,5'-dichloro-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N2'-(trans-4-(2-methoxyethylamino)cyclohexyl)-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 40 h / 20 - 120 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → trans-4-(2,5'-dichloro-5-((tetrahydro-2H-pyran-4-yl)methyl)amino-3,4'-bipyridin-2'-ylamino)cyclohexanol

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → trans-4-(2,5'-dichloro-5-((tetrahydro-2H-pyran-4-yl)methyl)amino-3,4'-bipyridin-2'-ylamino)cyclohexyl methanesulfonate

Conditions

Yield

Multi-step reaction with 5 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C 5: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N2'-(trans-4-((2-methoxyethyl)(methyl)amino)cyclohexyl)-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions

Yield

Multi-step reaction with 6 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: triethylamine / dimethyl sulfoxide / 72 h / 95 °C 5: triethylamine / dichloromethane / 2 h / 0 - 20 °C 6: tert-butyl alcohol / 5 h / 95 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N5-((tetrahydro-2H-pyran-4-yl)methyl)-N2'-(trans-4-(((R)-tetrahydrofuran-2-yl)methylamino)cyclohexyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: potassium carbonate / dimethyl sulfoxide / 9 h / 100 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N2'-(trans-4-(pyrrolidin-1-yl)cyclohexyl)-N5-((tetrahydro-2H-pyran-4-yl)methyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: dimethyl sulfoxide / 3 h / 100 °C 4: potassium carbonate / N,N-dimethyl-formamide / 3 h / 60 °C View Scheme

2-chloro-3-bromo-5-aminopyridine (130284-53-6) → 2,5'-dichloro-N5-((tetrahydro-2H-pyran-4-yl)methyl)-N2'-(trans-4-((R)-3,3,3-trifluoro-2-methoxypropylamino)cyclohexyl)-3,4'-bipyridine-2',5-diamine trifluoroacetate

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane / 20 h / 20 °C 2: sodium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 3 h / 100 °C / Inert atmosphere 3: 2,6-dimethylpyridine / dimethyl sulfoxide / 3 h / 135 °C View Scheme

Upstream product

• 15862-33-6 3-bromo-2-hydroxy-5-nitropyridine 
• 5470-17-7 3-bromo-2-chloro-5-nitropyridine 

Downstream Products

• 130115-85-4 5-bromo-6-chloropyridin-3-ol 
• 552330-65-1 6-chloro-5-[(E)-2-pyridin-4-ylvinyl]pyridin-3-amine 
• 130284-55-8 5-bromo-6-chloropyridin-3-yl acetate 
• 1131041-71-8 5-bromo-6-chloro-2-nitropyridin-3-ol 
• 1361852-33-6 3-bromo-2-chloro-5-trifluoromethoxy-pyridine 
• 1211586-80-9 3-bromo-2-chloro-5-iodopyridine 

Relevant articles and documents

3-(AMINOARYL)-PYRIDINE COMPOUNDS

The present invention provides a compound of formula (I): and pharmaceutically acceptable salts, enantiomers, stereoisomers, rotamers, tautomers, diastereomers, or racemates thereof. Also provided are pharmaceutical compositions containing these compounds and methods of treating a disease or condition mediated by CDK9 using these compounds and compositions.

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