911434-05-4

Basic information

• Product Name: 5-Bromo-2-methyl-3-nitropyridine
• Synonyms: 5-Bromo-2-methyl-3-nitropyridine;5-Bromo-3-nitropicoline;5-Bromo-2-methyl-3-nitrop...;5-Bromo-3-nitro-2-picoline;5-broMo-2-Methyl-3-n;Pyridine,5-broMo-2-Methyl-3-nitro-
• CAS NO: 911434-05-4
• Molecular Formula: C₆H₅BrN₂O₂
• Molecular Weight: 217.02
• EINECS: 200-258-5
• Product Categories: Heterocycle-Pyridine series
• Mol File: 911434-05-4.mol
• Article Data: 24

Chemical Properties

• Melting Point: 38.0 to 42.0 °C
• Boiling Point: 253 °C
• Flash Point: 107 °C
• Appearance: /
• Density: 1.709
• Vapor Pressure: 0.0305mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Room temperature.
• PKA: -0.44±0.20(Predicted)
• CAS DataBase Reference: 5-Bromo-2-methyl-3-nitropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-methyl-3-nitropyridine(911434-05-4)
• EPA Substance Registry System: 5-Bromo-2-methyl-3-nitropyridine(911434-05-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 911434-05-4(Hazardous Substances Data)

Usage

Uses

5-Bromo-2-methyl-3-nitropyridine is used as a reactant in the synthesis of MLN0905, a potent and orally bioavailable inhibitor of Polo-like kinase 1 (PLK1).

InChI:InChI=1/C6H5BrN2O2/c1-4-6(9(10)11)2-5(7)3-8-4/h2-3H,1H3

Synthetic route

2-(5-bromo-3-nitro-pyridin-2-yl)-malonic acid diethyl ester (911434-04-3) → 5-bromo-2-methyl-3-nitropyridine (911434-05-4)

Conditions	Yield
With hydrogenchloride; water for 5h; Heating / reflux;	96%
With hydrogenchloride In water Reflux;	95%
With hydrogenchloride; water for 5h; Reflux;	89.7%

5-bromo-2-chloro-3-nitropyridine (67443-38-3) + diethyl malonate (105-53-3) → 5-bromo-2-methyl-3-nitropyridine (911434-05-4)

Conditions	Yield
Stage #1: 5-bromo-2-chloro-3-nitropyridine; diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; for 3.5h; Stage #2: With hydrogenchloride; water Heating / reflux; Stage #3: With water; sodium carbonate pH=9;	63.3%
Stage #1: 5-bromo-2-chloro-3-nitropyridine; diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; for 3.5h; Stage #2: With hydrogenchloride; water Heating / reflux; Stage #3: With sodium carbonate pH=9;	63.3%
Stage #1: 5-bromo-2-chloro-3-nitropyridine; diethyl malonate With sodium hydride In tetrahydrofuran at 20℃; for 3.5h; Stage #2: With hydrogenchloride; water Heating / reflux; Stage #3: With water; sodium carbonate pH=9;	63.3%
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.333333h; Stage #2: 5-bromo-2-chloro-3-nitropyridine In N,N-dimethyl-formamide; mineral oil at 20 - 40℃; for 1.5h; Stage #3: With hydrogenchloride In water at 100℃; for 13h;
Stage #1: diethyl malonate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; Stage #2: 5-bromo-2-chloro-3-nitropyridine at 20 - 40℃; for 1.5h;

5-bromo-2-chloro-3-nitropyridine (67443-38-3) → 5-bromo-2-methyl-3-nitropyridine (911434-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 40 °C / Inert atmosphere 2: hydrogenchloride / water / 110 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 1.2: 2 h / 100 °C 2.1: hydrogenchloride; water / 18 h / Reflux 2.2: 0 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 100 °C 2.1: hydrogenchloride; water / 18 h / Reflux 2.2: 0 °C View Scheme

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → (E)-2-(5-bromo-3-nitropyridin-2-yl)-N,N-dimethylethen-1-amine (1229457-88-8)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 4h;	98%
In N,N-dimethyl-formamide at 90℃; for 4h;	76%
In N,N-dimethyl-formamide at 20 - 90℃; for 7.5h; Large scale;

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + 4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide → N-(6-methyl-5-nitropyridin-3-yl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide

Conditions	Yield
With potassium carbonate; rac-diaminocyclohexane; copper(I) bromide In toluene at 90 - 100℃; Reagent/catalyst; Solvent; Inert atmosphere;	96.3%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-(5-bromo-3-nitropyridin-2-yl)-N,N-dimethylethenamine (1227628-14-9)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 4.25h; Inert atmosphere;	95.2%
In N,N-dimethyl-formamide at 90℃; for 0.25h;	95.2%
In N,N-dimethyl-formamide at 10℃; for 5h;
In N,N-dimethyl-formamide at 100℃; for 1h;

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (877399-74-1) + 5-bromo-2-methyl-3-nitropyridine (911434-05-4) → tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate (1229457-95-7)

Conditions	Yield
Stage #1: 5-bromo-2-methyl-3-nitropyridine; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 20℃; for 0.333333h; Stage #2: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate With potassium carbonate In 1,2-dimethoxyethane; isopropyl alcohol at 20 - 85℃;	95%

(4,4,5,5-tetramethyl-2-[4-(methylsulfonyl)phenyl])-1,3,2-dioxaborolane (603143-27-7) + 5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 2-methyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1353715-51-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 12h; Inert atmosphere;	94%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + trimethylsilylacetylene (1066-54-2) → 2-methyl-3-nitro-5-[(trimethylsilyl)ethynyl]pyridine (1228962-69-3)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 80℃; for 4h;	91%

N,N-Dimethylpropargylamin (7223-38-3) + 5-bromo-2-methyl-3-nitropyridine (911434-05-4) → N,N-dimethyl-3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-amine (1286218-46-9)

Conditions	Yield
With diethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 20℃; for 15h; Product distribution / selectivity;	91%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃; Darkness; Reflux;	91%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 5-bromo-2-methylpyridin-3-ylamine (914358-73-9)

Conditions	Yield
With hydrogenchloride; iron In methanol; water for 2h; Reflux;	90%
With iron; ammonium chloride In ethanol; water at 90℃; for 0.666667h;	90%
With iron; ammonium chloride In ethanol; water at 90℃; for 0.666667h;	90%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + N-tert-Butoxycarbonyl-1-amino-3-propyne (92136-39-5) → tert-butyl [3-(6-methyl-5-nitropyridin-3-yl)prop-2-yn-1-yl]carbamate (1228962-84-2)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 70℃; for 2.5h; Inert atmosphere;	79%

1-methyl-piperazine (109-01-3) + 5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 1-methyl-4-(6-methyl-5-nitropyridin-3-yl)piperazine (1228962-94-4)

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 150℃; for 22h; sealed tube; Inert atmosphere;	71%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + C16H27BO → 5-(2-(cyclohex-3-en-1-yl)ethyl)-2-methyl-3-nitropyridine

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 45℃; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	67%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + bis(pinacol)diborane (73183-34-3) → 2-methyl-3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1353715-51-1)

Conditions	Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 100℃; for 1.5h; Microwave irradiation;	66%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 6h; Inert atmosphere;

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + C14H27BO2 → 5-(2-(t-butoxy)ethyl)-2-methyl-3-nitropyridine

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In water at 45℃; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	64%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + tert-butyl 3,3-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-dihydropyridine-1-carboxylate (1228962-22-8) → tert-butyl 3',3',6-trimethyl-5-nitro-3',6'-dihydro-3,4'-bipyridine-1'(2'H)-carboxylate (1228962-23-9)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 24h; Inert atmosphere;	60%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 6-bromo-1H-pyrrolo[3,2-b]pyrridine (944937-53-5)

Conditions	Yield
Stage #1: 5-bromo-2-methyl-3-nitropyridine; N,N-dimethyl-formamide dimethyl acetal In N,N-dimethyl-formamide at 100℃; for 1h; Stage #2: With iron; acetic acid at 100℃; for 20h; Inert atmosphere;	60%

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl )-1,2,3,6-tetrahydropyridine (454482-11-2) + 5-bromo-2-methyl-3-nitropyridine (911434-05-4) → C12H15N3O2

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; Inert atmosphere;	56%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + tert-butyl 4-methylidenepiperidine-1-carboxylate (159635-49-1) → tert-butyl 4-[(6-methyl-5-nitro-3-pyridyl)methylene]piperidine-1-carboxylate

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 100℃; Sealed tube;	42%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + 3-ethynyloxetan-3-ol (1352492-38-6) → 3-[2-(6-methyl-5-nitro-3-pyridyl)ethynyl]oxetan-3-ol

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine at 20℃;	40%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + vinyl magnesium bromide (1826-67-1) → 4-bromo-7-methyl-1H-pyrrolo[2,3-c]pyridine

Conditions	Yield
In tetrahydrofuran at -50 - -40℃; for 0.5h; Inert atmosphere;	36.6%
In tetrahydrofuran at -50 - -40℃; for 0.5h; Inert atmosphere;	36.6%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) + (2,2'-bipyride-kN1,kN1')(1,1,1-trifluoromethanethiolato-kS)-copper (1413732-47-4) → 2-methyl-3-nitro-5-[(trifluoromethyl)thio]pyridine

Conditions	Yield
In 1,4-dioxane at 110℃; for 15h; Inert atmosphere;	23%

5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 5-bromo-3-nitropicolinic acid (954240-89-2)

Conditions	Yield
With potassium permanganate In acetonitrile at 80 - 100℃;	2.4%

5-ethynylpyrimidine-2-amine (857265-74-8) + 5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 5-(6-methyl-5-nitro-pyridin-3-ylethynyl)-pyrimidin-2-ylamine (911434-06-5)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide at 60℃; for 3h;

5-bromo-2-methyl-3-nitropyridine (911434-05-4) → N-(6-(5-(4-methoxyphenylsulfonamido)-6-methylpyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (1112980-38-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: water; iron; acetic acid / 1.25 h / 20 °C / Inert atmosphere; Cooling 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate / 1,2-dimethoxyethane; water / 1.33 h / 100 °C / Inert atmosphere 3: pyridine; dmap / tetrahydrofuran / 6 h / 65 °C / Inert atmosphere View Scheme

5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 6-bromo-1H-pyrazolo[4,3-b]pyridine (1150617-54-1)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 3.2: 40 - 60 °C 3.3: 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2: triethylamine / dichloromethane / 90 h / 20 °C 3: acetic anhydride; potassium acetate; isopentyl nitrite / chloroform; acetic acid / 20 - 60 °C View Scheme
Multi-step reaction with 4 steps 1.1: acetic acid; iron / 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h 2.2: 1 h 3.1: acetic anhydride; potassium acetate; acetic acid; isopentyl nitrite / toluene / 3 h / Reflux 4.1: potassium carbonate; methanol / 1 h / Reflux View Scheme

5-bromo-2-methyl-3-nitropyridine (911434-05-4) → N-(5-bromo-2-methyl-pyridin-3-yl)-acetamide (1301214-71-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2: triethylamine / dichloromethane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2: triethylamine / dichloromethane / 90 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: acetic acid; iron / 2 h / Reflux 2.1: triethylamine / dichloromethane / 18 h 2.2: 1 h View Scheme

5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 1H-pyrazolo[4,3-b]pyridine-6-carboxylic acid methyl ester (1301214-72-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 3.2: 40 - 60 °C 3.3: 0 - 20 °C 4.1: triethylamine / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr View Scheme
Multi-step reaction with 4 steps 1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2: triethylamine / dichloromethane / 90 h / 20 °C 3: acetic anhydride; potassium acetate; isopentyl nitrite / chloroform; acetic acid / 20 - 60 °C 4: triethylamine / (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr View Scheme
Multi-step reaction with 4 steps 1: iron; ammonium chloride / water; ethanol / 0.17 h / 90 °C 2: acetic acid / 20 °C 3: acetic anhydride; isopentyl nitrite; potassium acetate / toluene / 90 °C / Inert atmosphere 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 100 °C / 7600.51 Torr View Scheme

5-bromo-2-methyl-3-nitropyridine (911434-05-4) → 1H-pyrazolo[4,3-b] pyridine-6-carboxylic acid (1256807-59-6)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogenchloride; iron / ethanol; water / 40 °C / Reflux 2.1: triethylamine / dichloromethane / 0 - 20 °C 3.1: acetic anhydride; potassium acetate; acetic acid / chloroform / 0.25 h / 20 °C 3.2: 40 - 60 °C 3.3: 0 - 20 °C 4.1: triethylamine / 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr 5.1: sodium hydroxide; water / methanol / 0 - 20 °C 5.2: pH 5 - 6 View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride; iron / water; industrial methylated spirit / 2 h / Reflux 2.1: triethylamine / dichloromethane / 90 h / 20 °C 3.1: acetic anhydride; potassium acetate; isopentyl nitrite / chloroform; acetic acid / 20 - 60 °C 4.1: triethylamine / (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium dichloride / acetonitrile / 18 h / 100 °C / 15001.5 Torr 5.1: sodium hydroxide; water / methanol / 18 h / 20 °C 5.2: pH 5 - 6 View Scheme
Multi-step reaction with 5 steps 1: iron; ammonium chloride / water; ethanol / 0.17 h / 90 °C 2: acetic acid / 20 °C 3: acetic anhydride; isopentyl nitrite; potassium acetate / toluene / 90 °C / Inert atmosphere 4: triethylamine; bis-triphenylphosphine-palladium(II) chloride / 100 °C / 7600.51 Torr 5: water; sodium hydroxide / 20 °C View Scheme

Upstream product

• 67443-38-3 5-bromo-2-chloro-3-nitropyridine 
• 105-53-3 diethyl malonate 
• 911434-04-3 2-(5-bromo-3-nitro-pyridin-2-yl)-malonic acid diethyl ester 

Downstream Products

• 1112980-38-7 N-(6-(5-(4-methoxyphenylsulfonamido)-6-methylpyridin-3-yl)benzo[d]thiazol-2-yl)acetamide 
• 1083326-22-0 N-(5-bromo-2-methyl-pyridin-3-yl)-2,4-difluoro-benzenesulfonamide 
• 1093819-39-6 N-(5-bromo-2-methyl-pyridin-3-yl)-methanesulfonamide 
• 1392099-63-6 N-{5-[4-ethyl-6-(6-methyl-pyridin-3-yl)-pyrimidin-5-ylethynyl]-2-methyl-pyridin-3-yl}-2,4-difluoro-benzenesulfonamide 
• 1392099-64-7 N-{5-[4-ethyl-6-(2-methyl-pyridin-4-yl)-pyrimidin-5-ylethynyl]-2-methyl-pyridin-3-yl}-2,4-difluoro-benzenesulfonamide 
• 1392099-65-8 2-chloro-N-{5-[4-ethyl-6-(2-methyl-pyridin-4-yl)-pyrimidin-5-ylethynyl]-2-methyl-pyridin-3-yl}-benzenesulfonamide 
• 1391979-15-9 2,4-difluoro-N-(2-methyl-5-trimethylsilanylethynyl-pyridin-3-yl)-benzenesulfonamide 
• 1391979-17-1 N-(5-ethynyl-2-methyl-pyridin-3-yl)-2,4-difluoro-benzenesulfonamide 
• 1391979-18-2 N-(5-ethynyl-2-methyl-pyridin-3-yl)-benzenesulfonamide 
• 1391979-19-3 N-(5-ethynyl-2-methyl-pyridin-3-yl)-2-fluoro-benzenesulfonamide 
• 1391979-20-6 N-(5-ethynyl-2-methyl-pyridin-3-yl)-4-fluoro-benzenesulfonamide 
• 1391979-24-0 N-[5-(4-chloro-6-ethyl-pyrimidin-5-ylethynyl)-2-methyl-pyridin-3-yl]-2,4-difluoro-benzenesulfonamide 
• 1391979-26-2 N-[5-(4-chloro-6-methyl-pyrimidin-5-ylethynyl)-2-methyl-pyridin-3-yl]-2,4-difluoro-benzenesulfonamide 
• 1391979-27-3 N-[5-(4-chloro-6-methyl-pyrimidin-5-ylethynyl)-2-methyl-pyridin-3-yl]-benzenesulfonamide 

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