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. 72093-04-0, name is 3-Chloro-4-methylpyridine, molecular formula is C6H6ClN, 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. Application In Synthesis of 3-Chloro-4-methylpyridine

To a solution of lithium diisopropylamide (3OmL, 2M in THF) at -70C is added under argon a solutionof 3-chloro-4-methylpyridine (6.3 8g, 1 eq, SOmmol) in 25mL THF. The mixture is stirred for 5mm at -70C and then allowed to reach -30C. Thereafter the mixture is cooled down to -70C and a solution of 2-chloro- 1 -(1 -chlorocyclopropyl)ethanone (9.1 8g, 1 .2eq, 6Ommol) in 25mL THF is added. Then the mixture is allowed to reach ambient temperature and stirred for lh. Thereafter the mixture is cooled to 0C and saturated aqueous ammonium chloride solution is added. After extraction with ethyl acetate and evaporation of the solvent the crude material is purified via column chromatography over silica gel (eluent cyclohexane / ethyl acetate gradient). After evaporation of the solvent 1 Og (73%) of 3 -chloro-4- { [2-( 1-chlorocyclopropyl)oxiran-2-yl]methyl}pyridine are obtained as colourless oil.

With the rapid development of chemical substances, we look forward to future research findings about 72093-04-0.

Reference:
Patent; BAYER CROPSCIENCE AG; HOFFMANN, Sebastian; SUDAU, Alexander; DAHMEN, Peter; WACHENDORFF-NEUMANN, Ulrike; BERNIER, David; LACHAISE, Helene; BRUNET, Stephane; VIDAL, Jacky; GENIX, Pierre; COQUERON, Pierre-Yves; GEIST, Julie; VORS, Jean-Pierre; KENNEL, Philippe; MILLER, Ricarda; WO2014/167008; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73406-50-5, Ethyl 3-hydroxypicolinate, 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 C8H9NO3, blongs to pyridine-derivatives compound. Computed Properties of C8H9NO3

EXAMPLE 2 Preparation of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate (Compound No. 2) To 0.5 g of 60% sodium hydride, 50 ml of hexane was added, and subjected to decantation. Then, the mixture was suspended in 30 ml of dimethylformamide. To the dimethylformamide suspension, 1.9 g of ethyl 3-hydroxypicolinate was gradually added, and the 2.0 g of 2-chloro-4,6-dimethoxypyrimidine was added. The mixture was heated and stirred at a reaction temperature of from 130 to 140 C. for 4 hours. After cooling, the reaction solution was poured into water, and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. Ethyl acetate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 1.4 g of ethyl 3-(4,6-dimethoxypyrimidin-2-yl)oxy picolinate. (Yield: 40%, pale yellow liquid, refractive index nD20 =1.5389)

The synthetic route of 73406-50-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4832729; (1989); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 22282-70-8 ,Some common heterocyclic compound, 22282-70-8, molecular formula is C5H3FIN, 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.

Reference Example 2; 4-iodopyridin-2-amine2-Fluoro-4-iodopyridine (11.2 g, 50 mmol) obtained in Reference Example 1 and 28% aqueous ammonia solution (100 ml) were stirred at 150 C. for 3 hr in a sealed tube. The mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous sodium hydrogensulfate. The solvent was evaporated under reduced pressure. The obtained residue was crystallized from ethyl acetate to give the title compound (6.6 g, yield 60%). melting point 167-168 C.1H-NMR (CDCl3) delta: 4.34 (2H, brs), 6.92 (1H, d, J=1.4 Hz), 6.99 (1H, dd, J=5.5, 1.4 Hz), 7.73 (1H, d, J=5.5 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-70-8, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2011/39893; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 920966-03-6, 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.920966-03-6, name is 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid, molecular formula is C8H5ClN2O2, molecular weight is 196.59, as common compound, the synthetic route is as follows.

Preparation 32To a solution of 4-chloro-lH-pyrrolo[2, 3-b]pyridine-5- carboxylic acid (840mg) inN,N-dimethylformamide (8.4mL) were added 1-hydroxybenzotriazole (808 mg) and 1- (3-dimethylaminopropyl) – 3-ethylcarbodiimide (929 mg) . The mixture was stirred at 600C for 30 minutes. The solution was cooled to ambient temperature and added EPO 28% ammonium hydroxide aqueous solution (1.2 ?iL) . The mixture was stirred at ambient temperature for 1 hour. To the solution were added water and chloroform and the mixture was extracted with chloroform.The extract was dried over MgSO4, filtrated and evaporated. The residue was purified by column chromatography on silica gel with chloroform and methanol (100:0 to 90:10) to give 4-chloro- lH-pyrrolo [2, 3-b]pyridine-5-carboxamide (90 mg) as a pale yellow powder.1H-NMR (DMSO-d6) delta : 6.55-6.57 (lH,m) , 7.63-7.66 (lH,m) , 7.90 (2H,br) ,8.2 9(lH,s) ,12.16(lH,brs) .MS (ESI) :m/z 218(M+Na)+.

Statistics shows that 920966-03-6 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid.

Reference:
Patent; ASTELLAS PHARMA INC.; WO2007/7919; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1060805-95-9, 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. 1060805-95-9, name is 4-Chloro-6-methylnicotinic acid, molecular formula is C7H6ClNO2, 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.

Step 2: A mixture of 4-chloro-6-methyl-3-pyridinecarboxylic acid (10 g, 58.4mmol) and KMnO4 (27.7 g, 175.4 mmol) in H2O was reflux with stirring for 24 h. The mixture was cooled to temperature and filtrated. EtOH was added to the filtrate and filtrated again. The filtrate was concentrated by vacuo to give the crude product 17 g which was used directly to the next reaction without further purification.

According to the analysis of related databases, 1060805-95-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; WANG, Yonghui; YU, Hongyi; WO2010/59552; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 127915-50-8, 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.127915-50-8, name is 4-Amino-6-methylnicotinic acid, molecular formula is C7H8N2O2, molecular weight is 152.15, as common compound, the synthetic route is as follows.

The cake is washed with ether and dried in vacuo. In a similar manner, starting with 4-amino-6-methylnicotinic acid, the corresponding 4-amino-5-bromo-6-methylnicotinic acid is prepared.

The chemical industry reduces the impact on the environment during synthesis 127915-50-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Pfizer Inc.; US3950160; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17570-98-8, 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.17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, molecular weight is 280.95, as common compound, the synthetic route is as follows.

7V,/V-dicyclopropyl-6-ethyl-l-methyl-4-(4-(pyridin-2-yl)thiazol-2-ylamino)-l,6- dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide [00183] A solution of 4-amino-N,N-dicyclopropyl-6-ethyl-l -methyl- 1,6- dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide (example 1J, 70 mg, 0.21 mmol) and benzoyl isothiocyanate (36 mu, 0.27 mmol) in acetone (1 ml) was stirred at room temperature for 1.5h. The solvent was removed in vacuo, the residue was taken up in EtOH (1.5 ml), and K2CO3 (40 mg, 0.290 mmol) was added. The reaction was heated at 60C for 3h. Upon cooling to room temperature, 2-bromo-l- (pyridin-2-yl)ethanone, hydrobromide (139.4 mg, 0.50 mmol) was added and the reaction heated at 80C for 24h. The reaction mixture was cooled to roomtemperature and concentrated. The residue was purified by silica gel chromatography (0-7% MeOH/dichloromethane). Re-purification by preparative HPLC provided 10.2 mg (10% yield) of N,N-dicyclopropyl-6-ethyl-l -methyl -4-(4-(pyridin-2-yl)thiazol-2- ylamino)-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide as a brown solid.[00184] MS (ESI) rt = 1.78 min, m/z 499 (M+H).[00185] 1H MR (DMSO-d6) delta ppm 10.9 (s, 1 H), 8.2 (bs, 1 H), 7.81 (d, 1 H), 7.75 (s, 1H), 3.92 (m, 4H), 3.77 (q, 2H, J= 7.8 Hz), 2.52-2.81 (m, 7H).

Statistics shows that 17570-98-8 is playing an increasingly important role. we look forward to future research findings about 2-(Bromoacetyl)pyridine hydrobromide.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PURANDARE, Ashok V.; GREBINSKI, James W.; HART, Amy; INGHRIM, Jennifer; SCHROEDER, Gretchen; WAN, Honghe; WO2011/28864; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 52378-63-9, name is (3-Aminopyridin-2-yl)methanol. A new synthetic method of this compound is introduced below., Formula: C6H8N2O

i. A solution sodium nitrite (2.28 g) in water (10 ml) was added dropwise to a stirred mixture of 3-amino-2-hydroxymethylpyridine (4.8 g) in aqueous hydrobromic acid (48%, 10 ml) and water (5 ml) at 0.5 C. This solution of the diazonium salt was added to a hot solution of cuprous bromide (2.5 g) in 60% hydromic acid and following cessation of nitrogen evolution the mixture was heated on the steam bath for 0.5 hours, diluted with water and saturated with hydrogen sulphide. Filtration, concentration to low bulk and extraction with chloroform yielded 3-bromo-2-hydroxymethylpyridine (4.8 g).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 52378-63-9, (3-Aminopyridin-2-yl)methanol.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4000302; (1976); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1060814-91-6, Ethyl 2-(4-bromopyridin-2-yl)acetate, 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, 1060814-91-6, blongs to pyridine-derivatives compound. Computed Properties of C9H10BrNO2

Step 2: 1 -(4-bromo-pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester; NaH (55% in mineral oil, 0.72 g) was added to a solution of (4-bromo-pyridin-2-yl)-acetic acid ethyl ester (1 .80 g) in N,N-dimethylformamide (20 mL) chilled in an ice bath. The resulting mixture was stirred for 10 min at room temperature and then cooled again in an ice bath. 1 ,2- Dibromoethane (0.70 mL) was added dropwise and the cooling bath was removed. The mixture was stirred at room temperature overnight. Brine was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgS04). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5?1 :1 ) to give the title compound as an oil. Yield: 1 .28 g (64% of theory); Mass spectrum (ESI+): m/z = 270/272 (Br) [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,1060814-91-6, its application will become more common.

Reference:
Patent; VITAE PHARMACEUTICALS, INC.; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LEFTHERIS, Katerina; ZHUANG, Linghang; TICE, Colin, M.; SINGH, Suresh, B.; YE, Yuanjie; XU, Zhenrong; HIMMELSBACH, Frank; ECKHARDT, Matthias; WO2011/159760; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 936011-17-5, Adding some certain compound to certain chemical reactions, such as: 936011-17-5, name is 5-Bromo-2-methoxyisonicotinaldehyde,molecular formula is C7H6BrNO2, 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 936011-17-5.

5-Bromo-2-methoxypyridine-4-carbaldehyde (25 g, 115.5 mmol, 1 eq.) Was dissolved in 500 ml of dichloromethane, and the temperature was lowered to -78 C. Under the protection of nitrogen,Diethylaminosulfur trifluoride (74.5g, 462mmol, 4eq.) Was added dropwise.After the dropwise addition, the reaction was carried out at 21 C for 16 hours.After the reaction, drop the reaction drop into ice water,Make alkaline with saturated sodium bicarbonate solution.It was extracted with dichloromethane, and the organic phase was concentrated and then subjected to column chromatography to obtain 25.3 g of white solid 5-bromo-4- (difluoromethyl) -2-methoxypyridine in 92% yield.

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. 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ali Biological New Materials (Changzhou) Co., Ltd.; Shi Jianyun; Xu Yibo; Dai Hongsheng; Zhou Chao; (8 pag.)CN110734397; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem