3430-26-0

Basic information

• Product Name: 2,5-Dibromo-4-methylpyridine
• Synonyms: TIMTEC-BB SBB003142;2,5-DIBROMO-4-METHYLPYRIDINE;2,5-DIBROMO-4-PICOLINE;2,3-dibromo-4-methylpyridine;2,5-Dibromo-4-picoline,98%
• CAS NO: 3430-26-0
• Molecular Formula: C₆H₅Br₂N
• Molecular Weight: 250.92
• EINECS: -0
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Pyridine Series;Halides;Boronic Acid;Brominated heterocyclic series
• Mol File: 3430-26-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 37-41 °C
• Boiling Point: 181.5°C (rough estimate)
• Flash Point: 112.7 °C
• Appearance: Light yellow to orange/Low Melting Solid
• Density: 1.9318 (rough estimate)
• Vapor Pressure: 0.0174mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: -0.91±0.18(Predicted)
• CAS DataBase Reference: 2,5-Dibromo-4-methylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dibromo-4-methylpyridine(3430-26-0)
• EPA Substance Registry System: 2,5-Dibromo-4-methylpyridine(3430-26-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-41-37/38-22
• Safety Statements: 36/37/39-26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3430-26-0(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow to orange low melting solid

InChI:InChI=1/C6H5Br2N/c1-4-2-6(8)9-3-5(4)7/h2-3H,1H3

Synthetic route

2,5-dibromopyridine (624-28-2) + methyl iodide (74-88-4) → 2,5-Dibromo-4-methylpyridine (3430-26-0)

Conditions	Yield
Stage #1: 2,5-dibromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: methyl iodide In tetrahydrofuran for 0.5h;	86%

2-amino-5-bromo-4-methylpyridine (98198-48-2) → 2,5-Dibromo-4-methylpyridine (3430-26-0)

Conditions	Yield
Stage #1: 2-amino-5-bromo-4-methylpyridine With hydrogen bromide; bromine; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: With sodium hydroxide In water at 20℃; pH=~ 13;	68%
Stage #1: 2-amino-5-bromo-4-methylpyridine With hydrogen bromide; bromine; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: With sodium hydroxide In water pH=~ 13;	68%

zinc(II) cyanide (557-21-1) + 2,5-Dibromo-4-methylpyridine (3430-26-0) → 5-bromo-4-methyl-pyridine-2-carbonitrile (886364-86-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 150℃; for 0.0833333h; Negishi Coupling; Microwave irradiation; regioselective reaction;	100%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 2,4,6-trivinylcyclotriboroxane*pyridine complex → 5-bromo-4-methyl-2-vinyl-pyridine (1122090-37-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 15h; Suzuki Coupling; Inert atmosphere;	99%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 15h; Suzuki Coupling;
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 80℃; for 15h; Inert atmosphere;

2,5-Dibromo-4-methylpyridine (3430-26-0) + cis-2,6-dimethylpiperazine (21655-48-1, 1013625-96-1) → (3S,5R)-1-(5-bromo-4-methylpyridin-2-yl)-3,5-dimethylpiperazine

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 110℃; for 18h;	96%

2,5-Dibromo-4-methylpyridine (3430-26-0) + sodium ethanolate (141-52-6) → 5-bromo-2-ethoxy-4-methylpyridine (610279-04-4)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 40 - 70℃; for 2h; Time;	95%

2,5-Dibromo-4-methylpyridine (3430-26-0) + m-tolylboronic acid (17933-03-8) → 2,5-(m-tolyl)-4-methylpyridine

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate In water; toluene for 16h; Inert atmosphere; Reflux;	93.3%

1-(1-methylethyl)piperazine (4318-42-7) + 2,5-Dibromo-4-methylpyridine (3430-26-0) → 1-(5-bromo-4-methylpyridin-2-yl)-3-isopropyl-piperazine (919496-46-1)

Conditions	Yield
With pyridine for 5h; Heating / reflux;	90%

2,5-Dibromo-4-methylpyridine (3430-26-0) + phenylboronic acid (98-80-6) → 5-bromo-4-methyl-2-phenylpyridine (31686-64-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 12h; Inert atmosphere;	90%
With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 50℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	82%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water Reflux;	77%

2,5-Dibromo-4-methylpyridine (3430-26-0) + phenylacetylene (536-74-3) → 5-bromo-4-methyl-2-(phenylethynyl)pyridine

Conditions	Yield
With copper(l) iodide; palladium(II) trifluoroacetate; palladium diacetate; diisopropylamine In methanol; acetonitrile for 24h; Reflux; Inert atmosphere; regioselective reaction;	90%

2,5-Dibromo-4-methylpyridine (3430-26-0) + phenylboronic acid (98-80-6) → 2,5-diphenyl-4-methylpyridine

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate In water; toluene for 16h; Inert atmosphere; Reflux;	87.2%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 90℃; for 12h; Schlenk technique; Inert atmosphere;	81%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In toluene at 120℃; for 2h; Inert atmosphere;	15.3 g

2,5-Dibromo-4-methylpyridine (3430-26-0) + acetonitrile (75-05-8) → (5-bromo-4-methyl-pyridin-2-yl)-acetonitrile

Conditions	Yield
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Metallation; Stage #2: 2,5-Dibromo-4-methylpyridine In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Alkylation;	86%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 3-Biphenylboronic acid (5122-95-2) → 2-([1,1'-biphenyl]-3-yl)-4,5-dimethylpyridine (1414352-90-1)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 18.33h; Inert atmosphere; Reflux;	85%

chloro-trimethyl-silane (75-77-4) + 2,5-Dibromo-4-methylpyridine (3430-26-0) → C9H14BrNSi

Conditions	Yield
Stage #1: 2,5-Dibromo-4-methylpyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 2h; Stage #2: chloro-trimethyl-silane In diethyl ether; hexane at -78 - 20℃; for 17h;	85%

2,5-Dibromo-4-methylpyridine (3430-26-0) + (tert-butyldimethylsilyl)acetylene (86318-61-8) → 5-bromo-2-((tert-butyldimethylsilyl)ethynyl)-4-methylpyridine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 2h; Inert atmosphere;	83.9%

2,5-Dibromo-4-methylpyridine (3430-26-0) + acetone (67-64-1) → 2-(5-bromo-4-methylpyridin-2-yl)propan-2-ol (1228014-47-8)

Conditions	Yield
Stage #1: 2,5-Dibromo-4-methylpyridine With n-butyllithium In hexane; toluene at -78℃; for 0.5h; Inert atmosphere; Stage #2: acetone at -78 - 20℃; for 2h;	82%
Stage #1: 2,5-Dibromo-4-methylpyridine With n-butyllithium In toluene at -78℃; Stage #2: acetone In toluene at -78 - 20℃; Stage #3: With water; ammonium chloride In toluene	63.5%
Stage #1: 2,5-Dibromo-4-methylpyridine With n-butyllithium In toluene at -78℃; for 1h; Stage #2: acetone In toluene at -78 - 20℃; for 1h;

2,5-Dibromo-4-methylpyridine (3430-26-0) + (2-aminopyrimidin-5-yl)boronic acid (936250-22-5) → 5-(5-bromo-4-methylpyridin-2-yl)pyrimidin-2-amine (1429341-51-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 2h;	82%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 2h;	82%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 4,4,5,5-tetramethyl-2-d5-phenyl[1,3,2]dioxaborolane → C12H5(2)H5BrN

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 50℃; for 18h;	81%
With palladium diacetate; potassium carbonate; triphenylphosphine In acetonitrile at 50℃; for 24h;	81%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 4-methylphenylboronic acid (5720-05-8) → 3-bromo-4-methyl-6-(p-tolyl)pyridine (1448777-16-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In methanol; acetonitrile at 60℃; for 4h; Inert atmosphere;	80%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 4-dibenzofurylboronic acid (100124-06-9) → 5-bromo-2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine (1414352-87-6)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water for 15h; Inert atmosphere; Reflux;	72%
In 1,2-dimethoxyethane; water; ethyl acetate	72%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water for 15h; Inert atmosphere; Reflux;	72%
With potassium carbonate; Pd(PPh3)4 In 1,2-dimethoxyethane; water; ethyl acetate	28.8 g (72%)

2-azetidinone (930-21-2) + 2,5-Dibromo-4-methylpyridine (3430-26-0) → 1-(5-bromo-4-methylpyridin-2-yl)azetidin-2-one

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 120℃; for 19.5h; Inert atmosphere; Molecular sieve; Sealed tube;	71%

2,5-Dibromo-4-methylpyridine (3430-26-0) + trivinylboroxin (92988-08-4) → 5-bromo-4-methyl-2-vinyl-pyridine (1122090-37-2)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 100℃; for 4h;	70%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h;	70%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h;	70%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h;	70%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 1-bromo-hexane (111-25-1) → 2,5-dibromo-4-heptylpyridine

Conditions	Yield
Stage #1: 2,5-Dibromo-4-methylpyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Schlenk technique; Stage #2: 1-bromo-hexane In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;	70%

2,5-Dibromo-4-methylpyridine (3430-26-0) + azetidine hydrochloride (78797-58-7, 78797-59-8, 78797-62-3, 36520-39-5) → 2-(azetidin-1-yl)-5-bromo-4-methylpyridine

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 90℃; for 20h;	66%

2,5-Dibromo-4-methylpyridine (3430-26-0) + C12H10Br2N2Te2 → 5,5'-dibromo-4,4'-dimethyl-2,2'-dipyridyl telluride

Conditions	Yield
Stage #1: C12H10Br2N2Te2 With sodium hydroxide; hydrazine hydrate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 2,5-Dibromo-4-methylpyridine In tetrahydrofuran; N,N-dimethyl-formamide for 24h; Heating;	65%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole (1218791-01-5) → 5-(5-bromo-4-methylpyridin-2-yl)-2-methylthiazole (1429341-63-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 3h;	64%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 3h;	64%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 2-methoxy-ethanol (109-86-4) → 5-bromo-2-(2-methoxyethoxy)-4-methylpyridine

Conditions	Yield
Stage #1: 2-methoxy-ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: 2,5-Dibromo-4-methylpyridine In tetrahydrofuran; mineral oil at 0 - 80℃;	61%
Stage #1: 2-methoxy-ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: 2,5-Dibromo-4-methylpyridine In tetrahydrofuran; mineral oil at 0 - 80℃;	61%
Stage #1: 2-methoxy-ethanol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: 2,5-Dibromo-4-methylpyridine In tetrahydrofuran; mineral oil at 0 - 80℃;	61%

2,5-Dibromo-4-methylpyridine (3430-26-0) + 4-Chlorophenylboronic acid (1679-18-1) → C12H9BrClN

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In ethanol; acetonitrile for 48h; Reflux;	61%

2,5-Dibromo-4-methylpyridine (3430-26-0) + (2-oxo-1,2-dihydropyridin-3-yl)boronic acid (951655-49-5) → 3-(5-bromo-4-methyl-2-pyridyl)-1H-pyridin-2-one

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 90℃; for 18h;	60.6%

sodium cyanide (773837-37-9) + 2,5-Dibromo-4-methylpyridine (3430-26-0) + copper(l) cyanide → 5-bromo-4-methyl-pyridine-2-carbonitrile (886364-86-9)

Conditions	Yield
In N,N-dimethyl-formamide at 158℃; for 3h; sealed vessel;	58%
In N,N-dimethyl-formamide for 20h; Reflux;	42.4%

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 74-88-4 methyl iodide 
• 98198-48-2 2-amino-5-bromo-4-methylpyridine 

Downstream Products

• 579475-84-6 3-[3-(6-ethyl-4-methyl-pyridin-3-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester 
• 31686-64-3 5-bromo-4-methyl-2-phenylpyridine 
• 1532554-35-0 C₄₆H₃₅IrN₄ 
• 610279-04-4 5-bromo-2-ethoxy-4-methylpyridine 
• 27063-92-9 5-bromo-2,4-dimethyl-pyridine 

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