Pyridine-derivatives

Application of 942473-59-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 942473-59-8, name is 2,5-Dibromoisonicotinic acid, molecular formula is C6H3Br2NO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 1; ethyl 2,5-dibromoisonicotinate (1-2)A solution of 2,5-dibromoisonicotinic acid (KL, 5 g, 17.80 mmol) and sulfuric acid (1.23 mL, 23.1 mmol)in ethanol (100 mL) was heated to reflux overnight. After reducing the volume of ethanol by rotary evaporation to approximately 1A of it’s original volume, the crude reaction mixture was partitioned between 2M sodium carbonate solution and EtOAc, separating layers and washing the organic layer with saturated sodium bicarbonate solution and brine. This solution was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase column chromatography (O to 50% EtOAc in hexanes) to afford the product (I1T) as a dark oil. ESI+ MS [M]+ C8H7Br2NO2 = 308.0.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 942473-59-8, 2,5-Dibromoisonicotinic acid.

Reference:
Patent; MERCK SHARP & DOHME CORP.; BERGMAN, Jeffrey, M.; COLEMAN, Paul, J.; MATTERN, Mamio Christa; MERCER, Swati, P.; REGER, Thomas, S.; ROECKER, Anthony, J.; WO2010/51236; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1849-52-1, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1849-52-1, name is 3-Methoxyisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Compound VI (23.8 g, 0.1 mol) was added to a 500 mL three-necked flask. Add tetrahydrofuran (100 mL), The stirring was started, and tetramethylpiperidine lithium (LTMP) (44 mL, 0.11 mol) was added dropwise at -40 ° C under nitrogen atmosphere. After the addition is completed, continue to stir for 0.5 hours. Then, a solution of 3-methoxy-4-pyridinecarboxaldehyde (13.7 g, 0.1 mol) in tetrahydrofuran was added dropwise. After the drop, continue to react at -40 ° C for 1 hour, TLC point plate monitoring,After the material point disappears, a saturated ammonium chloride solution is added dropwise below zero, and ethyl acetate is added. Extract, separate the organic layer, add anhydrous sodium sulfate to dry, filter,The filtrate was concentrated under reduced pressure.Obtained a yellow solid compound V-1, 32.9 g,The yield was 88percent.

According to the analysis of related databases, 1849-52-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Jin Yanjuan; (11 pag.)CN108689998; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 117873-72-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 117873-72-0, name is 2,6-Dibromo-4-methoxypyridine, molecular formula is C6H5Br2NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(1) Production of 2-bromo-4-methoxy-6-{3-(trifluoromethoxy)phenoxy} pyridine as an intermediate product 2.00 g (0.00937*1.2 mol) of 3-(trifluoromethoxy) phenol was dissolved in about 20 ml of dimethyl formamide. The solution was further mixed with 0.39 g (ca. 60% in mineral oil; 0.00937*1.04 mol) of sodium hydride and then with 2.50 g (0.00937 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 110 C. for about 4 hours, the mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed with hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluding solution: ethyl acetate/hexane), and the obtained product was subjected to recrystallization using hexane, thereby obtaining an aimed product. Yield by weight: 1.40 g; yield by percentage: 41%; oily substance; 1 H-NMR (60 MHz, CDCl3, delta): 3.73 (3H, s), 6.25 (1H, d, J=2 Hz), 6.69 (1H, d, J=2 Hz), 6.7-7.5 (4H, complex).

According to the analysis of related databases, 117873-72-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kureha Kagaku Kogyo Kabushiki Kaisha; US6005112; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 697739-12-1, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.697739-12-1, name is Ethyl imidazo[1,5-a]pyridine-8-carboxylate, molecular formula is C10H10N2O2, molecular weight is 190.2, as common compound, the synthetic route is as follows.

Ethyl imidazo [1, 5-a] pyridine-8-carboxylate (J. Het. CLIEIIZ., 1993,473) (0.21 g) was dissolved in 1M KOH in methanol (5 ml) and the solution heated at reflux for 5 min. The mixture was then concentrated, diluted with water (2 ml) and acidified to pH 1 with 2N HCI. The resulting precipitate was collected by filtration to give imidazo [1, 5-a] pyridine-8-carboxylic acid (80 mg) as a yellow solid.

Statistics shows that 697739-12-1 is playing an increasingly important role. we look forward to future research findings about Ethyl imidazo[1,5-a]pyridine-8-carboxylate.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2005/28445; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 63237-88-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 63237-88-7, name is Pyrazolo[1,5-a]pyridine-2-carboxylic acid, molecular formula is C8H6N2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 12N-[6-(1 H-lndol-4-yl)-1 H-indazol-4-yl]pyrazolo[1 ,5-a]pyridine-2-carboxamide Pyrazolo[1 ,5-a]pyridine-2-carboxylic acid (27 mg, 0.166 mmol) was treated with anhydrous THF (2ml) and then 1-chloro-N, N, 2-trimethylpropenylamine (0.026 ml, 0.20 mmol). The reaction was stirred at room temperature under nitrogen for 2 hrs. The reaction was then treated with anhydrous DIPEA (0.131 ml, 0.753 mmol) and 2ml of solution of 6-(1 H-indol-4-yl)-2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-4-amine (750mg, 2.26 mmol) in THF (30ml). The reaction was then stirred at room temperature under nitrogen for 69 hrs. The solvent was blown -off under a stream of nitrogen, dissolved in methanol (3ml) and then solvent removed under reduced pressure. The crude reaction mixture was dissolved in methanol (5ml), treated with Macroporous Tosic Acid (4.45 mmol/g, 102 mg, 0.45 mmol), stirred at room temperature for 17 hrs and then treated with 0.88 ammonia (0.5 ml), stirred for 30 minutes and then filtered. The solvent was removed under reduced pressure and then the residue purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound. LCMS (Method B) m/z 393 [MH+], R1 = 1.02min.

According to the analysis of related databases, 63237-88-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/147189; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

NaH (570 mg, 14.24 mmol) was added portion wise to stirred anhydrous DMSO (10 ml_). The mixture was heated to 80C until evolution of gas ceased and then cooled to 0C. A solution of (carbethoxymethyl)- triphenylphosphonium bromide (3.05 g, 7.12 mmol) in DMSO (10 ml_) was then added and the mixture stirred at r.t for 30 min. The mixture was cooled to 0C and a solution of 5-chloronicotinaldehyde (1 .0 g, 7.12 mmol) in DMSO (10 ml_) was added and the mixture was stirred at r.t for 1 h. The mixture was then poured into aqueous 1 M HCI and extracted into DCM (3 x 50 ml_). The organics were combined and washed with H2O (3 x 100 ml_) and brine (3 x 100 ml_), separated, dried (MgSO ) and concentrated. Purification by flash silica column chromatography (gradient elution /’-hex to 25% EtOAc in /-hex) gave the title compound as a yellow solid (1 .1 g, 57%). LCMS (ES+) 271 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; LUCKHURST, Christopher A.; HAUGHAN, Alan F.; BRECCIA, Perla; STOTT, Andrew J.; BURLI, Roland W.; HUGHES, Samantha J.; MUNOZ-SANJUAN, Ignacio; DOMINGUEZ, Celia; MANGETTE, John E.; WO2012/103008; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885168-04-7, 5-Bromo-3-chloropicolinaldehyde, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, HPLC of Formula: C6H3BrClNO, blongs to pyridine-derivatives compound. HPLC of Formula: C6H3BrClNO

5-Bromo-3-chloropicolylaldehyde 2.06 gAnd 1.00 g of 1-butylamineIn 10 ml of toluene,While performing azeotropic dehydration using a Dean-Stark tube,It was heated to reflux for 2 hours.Then,The solvent was distilled off under reduced pressure,To the residue was added acetic acid 10 mlAnd 1.05 g of nitroethane were added,Followed by stirring at 100 C. for 40 minutes.After completion of the reaction,The reaction mixture was allowed to cool to room temperature, 30 ml of water was added, and the mixture was extracted with ethyl acetate (50 ml × 2).The organic layers were combined, dried over anhydrous sodium sulfate and then saturated brine, dried,The solvent was distilled off under reduced pressure,The residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3: 97)0.76 g of the objective compound was obtained as brown crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885168-04-7, 5-Bromo-3-chloropicolinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; nissan chemical industries, Ltd.; Takeshi, Mita; Yuki, Tajima; Yusuke, Nanya; Kosay, Iwasa; Makoto, Inada; Miho, Asahi; (124 pag.)JP2017/39722; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Computed Properties of C5H3Cl2N3O2, blongs to pyridine-derivatives compound. Computed Properties of C5H3Cl2N3O2

(6) 2,4,6-trichloro-3-nitropyridine 2,6-dichloro-3-nitropyridine-4-amine (2.27 g, 10.9 mmol) was added to 48 mL concentrated hydrochloric acid, and cooled to 0-5 C. To the solution was added sodium nitrite (2.26 g, 32.7 mmol) in batches. After the addition of sodium nitrite, the reaction solution was stirred for 1 h at 0-5 C., and then stirred for 2 h at 25 C., adjusted to pH=7 with 40% sodium hydroxide solution, and extracted with ethyl ether. After the organic phase was dried (Na2SO4) and concentrated, it was subjected to column chromatography eluted with petroleum ether to afford 2 g white solid with a yield of 80.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2897-43-0, 2,6-Dichloro-3-nitropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; Xuanzhu Pharma Co., Ltd.; US2012/289497; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 114042-02-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 114042-02-3, name is 5-Bromo-3-methyl-2-nitropyridine, molecular formula is C6H5BrN2O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(1) Add DMA and DMF to the reaction kettle,The molar ratio of DMA to DMF is 2:3.Stir and mix well,Thereafter, 2-nitro-3-methyl-5-bromopyridine is added thereto.Heat, keep the temperature at 160 C,Carry out a reflux reaction,After the reaction is completed,Distilling the solvent under reduced pressure,Add absolute ethanol,After mixing evenly, suction filtration, washing,Drying2-nitro-3-dimethylamine vinyl-5-bromopyridine

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 114042-02-3, 5-Bromo-3-methyl-2-nitropyridine.

Reference:
Patent; Jiaxing Xiuzhou Qu Hong Hezhen Middle School; Zhu Shengxiang; (6 pag.)CN109456323; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66909-38-4, Adding some certain compound to certain chemical reactions, such as: 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine,molecular formula is C6H7ClN2, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 66909-38-4.

2-Chloro-4-methyl-5-nitropyridine (lg, 5.8 mmol) was dissolved in EtOH (60 mL). AcOH (4 mL) and Fe (5 eq. ) were added and the mixture was refluxed at 80C overnight. The mixture was filtered through celite and reduced under vacuum to afford the crude 5-amino-2-chloro-4-methylpyridine which was used in the next step with no further purification. The amine was dissolved in cone. HC1 (6 mL), transferred to a 3-neck round bottom flask, and cooled to-5 C. A solution of NaNO2/H2O (440 mgs/5 mL) was slowly added and the mixture was allowed to stir for 10 mins. To a second, separate 3-neck round bottom flask was added H20 (12 mL) and cooled to-5 C. Thionyl chloride (4.5 eq. ) was then added dropwise. After complete addition the mixture was allowed to warm to room temp. Whereupon CuCl (. 05 eq. ) was added and the mixture was then cooled back down to -5C. The first reaction mixture, containing the amine precursor, was slowly added to the second reaction mixture. A froth formed and was filtered off to afford 6-chloro-4-methyl-pyridine-3-sulfonyl chloride which was used in the next step with no further purification. The title compound was synthesized from 2- [2- (R, S)-3-oxo-1, 2,3, 4-tetrahydro-quinoxalin-2-yl]-N- (pyrid- 4-yl) ethyl acetamide and 6-chloro-4-methyl-pyridine-3-sulfonyl chloride using Method G. MS ni/z (M+H) 501.4 ; HPLC (CH3CN-H2O-0.1% TFA): Rt= 2.05 min.

According to the analysis of related databases, 66909-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2003/93245; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem