Category: pyridine-derivatives

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. 156094-63-2, name is 2-(Bromomethyl)-6-methoxypyridine, molecular formula is C7H8BrNO, 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. name: 2-(Bromomethyl)-6-methoxypyridine

To a 100-mL round-bottomed flask was added 2-(bromomethyl)-6- methoxypyridine (1.33 g, 6.58 mmol), 2-(bromomethyl)-6-methoxypyridine (1.33 g, 6.58 mmol), ethyl N-(diphenylmethylene) glycinate (1.76 g, 6.58 mmol, Acros, New Jersey) and 5N sodium hydroxide (6.58 mL, 32.9 mmol) in THF (30 mL). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2 x 50 mL). The organic extract was washed with saturated NaCl (30 mL) and dried over Na2S04. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 10% EtOAc/hexanes to give ethyl N- (diphenylmethylidene)-3-(6-methoxy-2-pyridinyl)alaninate (1.86 g) as a colorless oil.

With the rapid development of chemical substances, we look forward to future research findings about 156094-63-2.

Reference:
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael David; BO, Yunxin; BRYAN, Marian C.; CROGHAN, Michael; FOTSCH, Christopher Harold; HALE, Clarence Henderson; KUNZ, Roxanne Kay; LIU, Longbin; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis Dale; POON, Steve Fong; STEC, Markian Myroslaw; ST. JEAN, David, Joseph, Jr.; TAMAYO, Nuria A.; TEGLEY, Christopher Michael; YANG, Kevin Chao; WO2012/27261; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39856-57-0, name is 2,6-Dibromopyridin-3-amine, the common compound, a new synthetic route is introduced below. Recommanded Product: 39856-57-0

To a stirred solution of 2, 6-dibromopyridin-3-amine (38 g, 0.188 mol) in 1, 4- dioxane (400 mL) under an argon atmosphere was added sodium methoxide (70.55 g, 1.30 mol) at room temperature. The reaction mixture was stirred at reflux for 8 h. After consumption of the starting material (monitored by TLC), the reaction mixture was quenched with ice cold water (200 mL) and extracted with EtOAc (3 x 200 mL). The combined organic extracts were washed with cold water (2 x 100 mL), dried over sodium sulfate and concentrated in vacuo. The crude material was purified by column chromatography using 10% EtOAc:hexanes to afford 6-bromo-2-methoxypyridin-3-amine (13 g, 42%) as a brown solid. 1H-NMR (CDCl3, 400 MHz): delta 6.87 (d, 1H), 6.76 (d, 1H), 4.01 (s, 3H), 3.75 (br s, 2H); TLC: 20% EtOAc:hexane (Rf: 0.5).

The synthetic route of 39856-57-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/109109; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58602-02-1, Adding some certain compound to certain chemical reactions, such as: 58602-02-1, name is 2,6-Difluoro-3-nitropyridine,molecular formula is C5H2F2N2O2, 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 58602-02-1.

Synthesis of 2,6-difluoro-3-aminopyridine 2,6-Difluoro-3-nitropyridine (3.84 g) was dissolved in ethanol (42 ml). A solution of iron powder (4.03 g) and ammonium chloride (2.57 g) in water (14 ml) was added, and the reaction solution was heated and stirred at 80C for one hour. After leaving to cool, the reaction solution was filtered through celite. Ethyl acetate and water were added and the organic layer was separated. The resulting organic layer was washed with brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (2.06 g). The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 3.66 (brs, 2H), 6.65 (dd, J=8.2, 3.0Hz, 1H), 7.22 (ddd, 10.4, 8.2, 6.8Hz, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 58602-02-1, 2,6-Difluoro-3-nitropyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 23628-31-1, name is 6-Aminopicolinic acid, the common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Aminopicolinic acid

To a solution of 2-amino-6-pyridinecarboxylic acid (90; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 91 (5.5 g, 76%).

The synthetic route of 23628-31-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; VU, Chi, B.; DISCH, Jeremy, S.; NG, Pui, Yee; BLUM, Charles, A.; PERNI, Robert, B.; WO2010/3048; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 36178-05-9, 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. 36178-05-9, name is 3-Bromo-2-fluoropyridine, molecular formula is C5H3BrFN, 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.

A 60% dispersion of sodium hydride in mineral oil (7.4 g, 184.6 mmol) was suspended in anhydrous tetrahydrofuran (300 mL) under nitrogen. Absolute ethanol (10.0 mL, 170.4 mmol) was added dropwise at room temperature and the reaction mixture was stirred for 40 minutes at room temperature. 2-Fluoro-3-bromopyridine (25.0 g, 142.0 mmol) was added and the reaction mixture was stirred for 3 hours at room temperature. Water (250 mL) was added and the organic layer was separated. The aqueous layer was extracted with ethyl acetate (2 x 200 mL). The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a light yellow oil (31 .5 g, 84%). 1H NMR (400MHz, CDCl3): delta ppm 1.43 (m, 3H), 4.43 (m, 2H), 6.74 (m, 1 H), 7.79 (m, 1 H), 8.07 (m, 1 H). LCMS Rt = 2.45 minutes MS m/z 203 [MH]+

According to the analysis of related databases, 36178-05-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; STORER, Robert, Ian; SWAIN, Nigel, Alan; WO2013/93688; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20511-12-0 ,Some common heterocyclic compound, 20511-12-0, molecular formula is C5H5IN2, 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.

Step 1 : 5-(Methylthio)-2-pyridinamine (199) To a stirred solution of 2-amino-5-iodopyridine (1 1.6 g, 52.6 mmol) in MeOH (250 ml.) was added sodium thiomethoxide (5.16 g, 73.6 mmol) and copper powder (1.07 g, 16.8 mmol) at RT. The reaction mixture was heated in a sealed tube at 120 0C for 68 h. The reaction mixture was then cooled to RT and filtered through a pad of Celite. The Celite was rinsed with MeOH and the combined organics were concentrated under reduced pressure and redissolved in EtOAc. The organic layer was washed with water (1 x 50 ml.) and the aqueous layer was extracted with EtOAc (2 x 100 ml_). The combined organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give 6.23 g (84%) of the title product 199 as an off-white solid. 1H NMR (400 MHz, CDCI3): delta 8.09 (s, 1 H), 7.51 – 7.48 (m, 1 H), 6.48 – 6.45 (m, 1 H), 4.35 (br s, 2 H), 2.38 (s, 3 H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 20511-12-0, 5-Iodopyridin-2-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/8895; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 16744-81-3, 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.16744-81-3, name is 4-Methoxypicolinaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.

A mixture of 45 G of 4-METHOXYPYRIDINE-2-CARBALDEHYDE (Ashimori et AL., Chem. Pharm. Bull. 38, 2446- 2458 (1990) ), 75.80 G of pyridine hydrochloride, 102.45 G of monomethyl malonate potassium salt and 4.1 mi of piperidin in 700 ML of pyridine are slowly heated, with stirring, to 120 C. When the evolution of gas starts, the heating source is temporarily removed to stop the reaction from becoming too violent. Once the reaction has subsided, the mixture is stirred at 120 C for a further 2.5 h, and the pyridine is then distilled off under reduced pressure. The residue is partitioned between ethyl acetate/water and the organic phase is washed with water and dried. The residue obtained after concentration is chroma- tographed on a silica gel column using ethyl ACETATE/PETROLEUM ether 2: 1. This initially gives 43.2 G of the title compound as a yellow oil which crystallizes on standing and then shows a m. p. of 80-82 C. The mass spectrum shows the molecular peak MHD AT 194 DA.

Statistics shows that 16744-81-3 is playing an increasingly important role. we look forward to future research findings about 4-Methoxypicolinaldehyde.

Reference:
Patent; ALTANA PHARMA AG; WO2004/76451; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.846036-96-2, name is (4-Amino-6-chloropyridin-3-yl)methanol, molecular formula is C6H7ClN2O, molecular weight is 158.59, as common compound, the synthetic route is as follows.HPLC of Formula: C6H7ClN2O

(4-Amino-6-chloropyridin-3-yl)methanol (2.6 g, 16.4 mmol) was dissolved in DCM (80 mL) along with Mn02 (14.3 g). The mixture was stirred at rt for 24 h. Mn02 was filtered off andthe filtrate was concentrated to afford 4-amino-6-chloronicotinaldehyde (1.67 g, 65%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,846036-96-2, (4-Amino-6-chloropyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; PRINCIPIA BIOPHARMA, INC.; VERNER, Erik; BRAMELD, Kenneth Albert; WO2015/120049; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 72587-18-9 ,Some common heterocyclic compound, 72587-18-9, molecular formula is C6H4ClF3N2, 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.

(4) 2.50 g of 6-chloro-3- (ethanesulfonyl) pyridine-2-carboxylic acid,And 30 mL of toluene were added 1.31 g of thionyl chloride,And one drop of DMF were heated under reflux for 3 hours.The reaction mixture was concentrated and dissolved in 30 mL of tetrahydrofuran, and under ice cooling,1.97 g of 3-amino-2-chloro-5- (trifluoromethyl) pyridine,And triethylamine (1.10 g) were added dropwise thereto.After stirring at room temperature for 3 hours,The reaction mixture was added to ice water and extracted with ethyl acetate.The obtained organic layer was washed with saturated brine,After drying over anhydrous magnesium sulfate, it was concentrated.The residue was subjected to silica gel column chromatography,2.4 g of Intermediate 36 described below was obtained.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 72587-18-9, 2-Chloro-5-(trifluoromethyl)pyridin-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical; Ikari, Kaori; (123 pag.)JP2019/6686; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 63572-73-6, 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 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine. This compound has unique chemical properties. The synthetic route is as follows.

10% Palladium on carbon (40 mg) was added to a solution of 5-nitro-1H-pyrazolo[3,4-b]pyridine (A) (308 mg, 1.876 mmol) in ethanol and tetrahydrofuran and the mixture was charged with H2 (gas). After stirring the reaction mixture for 15 h, the mixture was filtered using celite and purified by column chromatography. The desired product 1H-pyrazolo[3,4-b]pyridin-5-amine (B) (73 mg) was obtained as 89% yield.

According to the analysis of related databases, 63572-73-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29995; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem