3430-23-7

Usage

Uses

Used in Organic Synthesis:
3,5-Dibromo-4-methylpyridine is utilized as a building block in organic synthesis for its ability to facilitate the creation of a variety of complex organic molecules. Its structural features make it a valuable component in the synthesis of advanced organic compounds.
Used in Pharmaceutical Research:
In pharmaceutical research, 3,5-Dibromo-4-methylpyridine is employed as a precursor for the synthesis of biologically active compounds. Its unique chemical properties allow it to be a key intermediate in the development of new pharmaceuticals with potential therapeutic applications.
Used in Drug Development:
3,5-Dibromo-4-methylpyridine is used as a starting material in the production of potential drugs. Its chemical structure provides a foundation for the design and synthesis of novel drug candidates that can address unmet medical needs.
Used in Agrochemical Production:
3,5-Dibromo-4-methylpyridine also serves as a starting material for the development of agrochemicals, contributing to the creation of new products for agricultural applications, such as pesticides and herbicides.
Used in Antimicrobial Applications:
3,5-Dibromo-4-methylpyridine is used as an antimicrobial agent due to its inherent ability to combat microbial infections. This property makes it a candidate for the development of new treatments against resistant bacteria and other pathogens.
Used in Anti-inflammatory Applications:
3,5-Dibromo-4-methylpyridine's anti-inflammatory properties position it as a potential agent for the treatment of inflammation-related conditions. Its use in this context could lead to the development of new therapeutics for various inflammatory diseases.

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

Synthetic route

3,5-dibromopyridine (625-92-3) + methyl iodide (74-88-4) → 3,5-dibromo-4-methyl-pyridine (3430-23-7)

Conditions	Yield
Stage #1: 3,5-dibromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran at -78 - 20℃; for 18h;	66%
Stage #1: 3,5-dibromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - -10℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #1: 3,5-dibromopyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: methyl iodide In tetrahydrofuran at -78℃;

3,5-dibromopyridine (625-92-3) + methyl iodide (74-88-4) → 3,5-dibromo-4-methyl-pyridine (3430-23-7) + 3,5-dibromo-4-ethylpyridine (125419-80-9)

Conditions	Yield
With lithium diisopropyl amide 1.) THF, -78 deg C, 5 min; 2.) THF, -78 deg C, excess MeI; Yield given. Multistep reaction. Yields of byproduct given;

3,5-dibromopyridine (625-92-3) + methyl iodide (74-88-4) → 3,5-dibromo-4-methyl-pyridine (3430-23-7) + 3,5,3',5'-Tetrabromo-1,4-dihydro-[4,4']bipyridinyl

Conditions	Yield
With lithium diisopropyl amide 1.) THF, -78 deg C, 5 min; 2.) -78 deg C, 2h; Yield given. Multistep reaction;

methyl iodide (74-88-4) → 3,5-dibromo-4-methyl-pyridine (3430-23-7)

Conditions	Yield
Stage #1: 3,5-dibromopyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - -10℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; hexane at -78℃; for 2h;

3,5-dibromo-4-methyl-pyridine (3430-23-7) + carbonic acid dimethyl ester (616-38-6) → C8H7Br2NO2

Conditions	Yield
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: carbonic acid dimethyl ester In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	93%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + 2.3-dihydro-1,4-benzodioxin-6-ylboronic acid → C14H12BrNO2

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; for 16h; Inert atmosphere;	80%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + [3-(hydroxymethyl)phenyl]boronic acid (87199-15-3) → a-[3-(5-Bromo-4-methyl-pyridin-3-yl)-phenyl]-methanol (351458-12-3)

Conditions	Yield
	79%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 5-bromo-4-methyl-pyridine-3-carbaldehyde (351457-86-8)

Conditions	Yield
Stage #1: 3,5-dibromo-4-methyl-pyridine With n-butyllithium In tetrahydrofuran; hexane at -100℃; for 0.0833333h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -100 - -78℃; for 1.33333h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water Saturated solution;	72%
Stage #1: 3,5-dibromo-4-methyl-pyridine With n-butyllithium at -78℃; Stage #2: N,N-dimethyl-formamide Further stages.;

3,5-dibromo-4-methyl-pyridine (3430-23-7) + phenylboronic acid (98-80-6) → C12H10BrN

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;	71%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + potassium vinyltrifluoroborate → C8H8BrN

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine In ethanol at 90℃; for 4h; Suzuki Coupling; Inert atmosphere;	66%

3,5-dibromo-4-methyl-pyridine (3430-23-7) → 3,5-diiodo-4-methyl-pyridine (98139-01-6)

Conditions	Yield
With copper(l) iodide; potassium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 130℃; for 16h;	65%
With copper(l) iodide; potassium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 110℃; for 16h; Inert atmosphere;
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane Reflux;

3,5-dibromo-4-methyl-pyridine (3430-23-7) + 1-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)phenyl]pyrrolidin-2-one (1003309-09-8) → 1-(4-(5-bromo-4-methylpyridin-3-yl)phenyl)pyrrolidin-2-one

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; for 3h; Inert atmosphere;	63%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + Ethyl isobutyrate (97-62-1) → 1-(3,5-dibromopyridin-4-yl)-3-methylbutan-2-one

Conditions	Yield
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 1.16667h; Inert atmosphere; Stage #2: Ethyl isobutyrate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	63%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + carbon dioxide (124-38-9) → 5-bromo-4-methylpyridine-3-carboxylic acid (677702-58-8)

Conditions	Yield
Stage #1: 3,5-dibromo-4-methyl-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 20℃; for 1h;	53%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + methylamine (74-89-5) → 5-bromo-N,4-dimethylpyridin-3-amine

Conditions	Yield
With copper In 1,4-dioxane at 100℃; for 5h;	50%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + ethyl 2-cyanoacetate (105-56-6) → 5-bromo-4-methylnicotinonitrile (890092-52-1)

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; palladium diacetate; sodium hydride; 1,2-bis-(diphenylphosphino)ethane; potassium iodide In N,N-dimethyl-formamide at 130℃; for 22h; Inert atmosphere;	48%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + tert-butyl 4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate (470478-90-1) → tert-butyl 4-(4-(5-bromo-4-methylpyridin-3-yl)phenyl)piperazine-1-carboxylate

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate monohydrate In 1,4-dioxane; water at 85℃; Suzuki-Miyaura Coupling;	47%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + 4-methoxyphenylboronic acid (5720-07-0) → 3-bromo-5-(4-methoxyphenyl)-4-methylpyridine (885681-79-8)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 80℃; for 4h;	46%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline (1021868-08-5) → 5-(5-bromo-4-methylpyridin-3-yl)quinoline

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	41.2%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + 2-(3-ethoxy-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-bromo-5-(3-ethoxy-4-methoxyphenyl)-4-methylpyridine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; potassium carbonate In 1,4-dioxane; water at 120℃; for 2h; Inert atmosphere;	35%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + ethyl bromoacetate (105-36-2) → ethyl 3-(3,5-dibromopyridin-4-yl)propanoate (1440520-08-0)

Conditions	Yield
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: ethyl bromoacetate In tetrahydrofuran at -78℃; for 3h;	33.5%
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: ethyl bromoacetate In tetrahydrofuran at -78℃; for 2.5h; Inert atmosphere;	33%
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran at -78 - -70℃; for 0.5h; Inert atmosphere; Stage #2: ethyl bromoacetate In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;	32%
Stage #1: 3,5-dibromo-4-methyl-pyridine With lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - -70℃; for 0.5h; Inert atmosphere; Stage #2: ethyl bromoacetate In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere;	32%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + tetramethylstannane (594-27-4) → 3,4,5-trimethylpyridine (20579-43-5)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In toluene for 18h; Heating;	33%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + 5-methylisoindolin-1-one (65399-03-3) → 2-(5-bromo-4-methylpyridin-3-yl)-5-methylisoindolin-1-one (1231891-05-6)

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In 1,4-dioxane at 100℃; for 15h;	30%

trimethyl(prop-1-ynyl)silane (6224-91-5) + 3,5-dibromo-4-methyl-pyridine (3430-23-7) → 3-bromo-4-methyl-5-(prop-1-ynyl)pyridine (1383985-19-0)

Conditions	Yield
copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran; toluene at 70℃; Inert atmosphere;	16%

3,5-dibromo-4-methyl-pyridine (3430-23-7) + butyraldehyde (123-72-8) → 1-(5-Bromo-4-methyl-pyridin-3-yl)-butan-1-ol

Conditions	Yield
With n-butyllithium 1.) THF, -100 deg C, 4 min; 2.) 1 h, -78 deg C; Yield given. Multistep reaction;

3,5-dibromo-4-methyl-pyridine (3430-23-7) → 5-[3-[4-methoxymethyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-4-methyl-pyridine-3-carbaldehyde (916326-88-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / -78 °C 2: 69 percent / Pd(PPh3)4 / 90 °C View Scheme

3,5-dibromo-4-methyl-pyridine (3430-23-7) → C36H53N7O3Si2

Conditions	Yield
Multi-step reaction with 3 steps 1: n-BuLi / -78 °C 2: 69 percent / Pd(PPh3)4 / 90 °C 3: 99 percent / NaBH4 View Scheme

3,5-dibromo-4-methyl-pyridine (3430-23-7) → ethyl-{5-[3-(4-methoxymethyl-1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-4-methyl-pyridin-3-ylmethyl}-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: n-BuLi / -78 °C 2: 69 percent / Pd(PPh3)4 / 90 °C 3: 99 percent / NaBH4 4: 38 percent / aq. HCl / ethanol View Scheme

3,5-dibromo-4-methyl-pyridine (3430-23-7) → 2-{4-[1-(3,4-bis-difluoromethoxy-phenyl)-2-(3,5-dimethyl-pyridin-4-yl)-ethyl]-phenyl}-1,1,1,3,3,3-hexafluoro-propan-2-ol

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 33 percent / PdCl2(PPh3)2 / toluene / 18 h / Heating 2.1: LDA; HMPA / tetrahydrofuran / 0.5 h / -78 °C 2.2: 28 percent / HMPA / tetrahydrofuran / 3 h / -78 °C 3.1: TBAF / tetrahydrofuran / 6 h / 65 °C View Scheme

Upstream product

• 625-92-3 3,5-dibromopyridine 
• 74-88-4 methyl iodide 

Downstream Products

• 20579-43-5 3,4,5-trimethylpyridine 
• 351457-86-8 5-bromo-4-methyl-pyridine-3-carbaldehyde 
• 524775-16-4 4-(2-(3,4-bis-difluoromethoxy-phenyl)-2-{4-[2,2,2-trifluoro-1-trifluoromethyl-1-(2-trimethylsilanyl-ethoxymethoxy)-ethyl]-phenyl}-ethyl)-3,5-dimethyl-pyridine 
• 351458-12-3 a-[3-(5-Bromo-4-methyl-pyridin-3-yl)-phenyl]-methanol 
• 70201-49-9 3-bromo-5-methoxy-4-methylpyridine 
• 890092-52-1 5-bromo-4-methylnicotinonitrile 
• 1404367-13-0 3-bromo-5-cyclopropyl-4-methylpyridine 
• 1428651-90-4 4-bromo-5,6-dihydro-7H-cyclopenta[c]pyridin-7-one 
• 40041-96-1 angustine 
• 40041-95-0 angustoline 
• 40041-95-0 (+)-angustoline 
• 677702-58-8 5-bromo-4-methylpyridine-3-carboxylic acid 

Relevant academic research and scientific papers

Towards redox-switchable organocatalysts based on bidentate halogen bond donors

Redox-active bidentate halogen bond donors based on halopyridinium groups as halogen-bond donating units were synthesized and their structures were elucidated by X-ray diffraction analyses and DFT calculations.Viareversible twofold reduction, these dicationic species can be transformed to neutral compounds which should be much weaker Lewis acids. The corresponding electrochemical data were obtained, and CV as well as UV-vis and NMR techniques were also used to determine binding constants of these halogen bond donors to halides. While all titrations agree on the relative order of binding strengths (with chloride being bound strongest), there are marked deviations in the overall affinity constants which are discussed. In contrast to earlier azo-bridge analogues, the ethylene-linked variants presented herein do not oxidize halides, and thus the novel halogen bond donors could also be used as Lewis acidic organocatalysts in a halide abstraction benchmark reaction, yielding a performance similar to bis(haloimidazolium)-derived catalysts.

BENZENE COMPOUND HAVING 2 OR MORE SUBSTITUENTS

A superior LXR modulator is provided. A compound represented by the general formula (I): [wherein R1: -COR9 (wherein R9: alkyl, optionally substituted alkoxy or optionally substituted amino); R2: H, OH, alkoxy, optionally substituted amino, etc.; R3: H, optionally substituted alkyl, cycloalkyl, optionally substituted alkoxy, optionally substituted amino, halogeno, etc.; R4 and R5: H, optionally substituted alkyl, halogeno, etc.; R6 and R7: H, alkyl; R8: -X2R10 [wherein R10: -COR11 (wherein R11 : OH, optionally substituted alkoxy, optionally substituted amino, etc.), -SO2R12 (wherein R12: optionally substituted alkyl, optionally substituted amino, etc.), tetrazol-5-yl, etc.; X2: single bond, optionally substituted alkylene, etc.]; X1: -NH-, -O-, -S-, etc.; Y1: optionally substituted phenyl, optionally substituted 5- to 6-membered aromatic heterocyclyl; Y2: optionally substituted aryl, optionally substituted heterocyclyl, etc.] and the like is provided.

INDAZOLECARBOXAMIDE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF MALARIA

The invention relates to methods of treating or preventing malaria which comprises administering to a patient in need thereof, an effective amount of a 1H-indazole-3-carboxamide derivative of general formula (I), in the form of a base or of an addition salt with an acid, or in the form of a hydrate or of a solvate of said base or acid addition salt.

Indazolecarboxamide derivatives, preparation and use thereof as CDK1, CDK2 and CDK4 inhibitors

Compound corresponding to general formula (I): [image] in which, R1 represents a hydrogen or halogen atom, an NH2, NHR2, NHCOR2, NO2, CN, CH2NH2 and CH2NHR2; or alternatively R1 represents an optionally substituted phenyl or an optionally substituted heteroaromatic group; Ar represents an optionally substituted phenyl group or an optionally substituted heteroaromatic group; n represents 0, 1, 2 or 3; in the form of a base, of an addition salt with an acid, of a hydrate or of a solvate. Application in therapy.

Indazole compounds, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation

Indazole compounds that modulate and/or inhibit cell proliferation, such as the activity of protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating, e.g., kinases-dependent diseases to modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.

Substituted 4-(2,2-Diphenylethyl)pyridine-N-oxides as phosphodiesterase-4 inhibitors: SAR study directed toward the improvement of pharmacokinetic parameters

A detailed SAR study directed toward the optimization of pharmacokinetic parameters for analogues of L-791,943 is reported. The introduction of a soft metabolic site on this structure permitted the identification of L-826,141 as a potent phosphodiesterase type 4 (PDE4) inhibitor that is well absorbed and that presents a shorter half-life than L-791,943 in a variety of animal species. The efficacy of L-826,141 is also demonstrated in different in vivo models.

Synthesis of 4-alkyl-3,5-dibromo-, 3-bromo-4,5-dialkyl- and 3,4,5-trialkylpyridines via sequential metalation and metal-halogen exchange of 3,5-dibromopyridine

Lithiation of 3,5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3,5-dibromopyridines 2 in high yield. 3-Bromo-4,5-dialkylpyridines 3 were synthesized by metal-halogen exchange of 2 with one equivalent n-BuLi and reaction with a second electrophile. Further metal-halogen exchange of 3 and reaction with a third electrophile provided 3,4,5-trisubstituted pyridines 4.