Tag: M.W:100-200

Synthetic Route 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.

To a mixture of compound B-141 (8.0 g, 49 mmol) in anhydrous tetrahydrofuran (80 mL) was added DIBAL-H (98 mL, 1 M in hexane) dropwise at -78 C. The mixture was stirred at -78 C for 2 hours until TLC showed the reaction was complete. The reaction was quenched with 50 mL of aqueous saturated ammonium chloride solution at 0 C and filtered, and the filtrate was concentrated in vacuo to give compound B-142 (5.7 g, crude) as a brown oil. The crude product was used for the next step without any further purification.

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 63237-88-7, Pyrazolo[1,5-a]pyridine-2-carboxylic acid.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; MCRINER, Andrew, J.; WO2015/66371; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 127406-55-7, 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. 127406-55-7, name is 4-Pyridin-3-yl-benzaldehyde, molecular formula is C12H9NO, 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.

[4-(6-Ethyl-thieno[2,3-d]pyrimidin-4-yl)-piperazin-1-yl]-(4-pyridin-3-yl-phenyl)-methanone The target acid was obtained (50 mg) by essentially following Step 1 of Example 437 using 4-pyridin-3-yl-benzaldehyde in place of 4-pyridin-4-yl-benzaldehyde. ES-MS: (M+H)+200

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 127406-55-7, 4-Pyridin-3-yl-benzaldehyde.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2003/153556; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, 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, Application In Synthesis of Imidazo[1,2-a]pyridine-2-carboxylic acid, blongs to pyridine-derivatives compound. Application In Synthesis of Imidazo[1,2-a]pyridine-2-carboxylic acid

To a solution of 23-1 (O.lg, 0.7mmol) in EtOH (15ml) in a dried flask was added Pt2O (O. Ig, 0.4mmol). The reaction mixture was placed under a nitrogen atmosphere and was subsequently evacuated. This was repeated 3 times before placing the reaction mixture under an atmosphere of hydrogen. After 3h the reaction mixture was filtered through celite. Upon solvent removal the desired product 23-2 was obtained as an off-white powder. MS calculated M+H: 167.2, found 167.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK & CO., INC.; WO2006/135627; (2006); A2;,
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.17282-01-8, name is 3-Bromo-2-fluoro-5-picoline, molecular formula is C6H5BrFN, molecular weight is 190.01, as common compound, the synthetic route is as follows.Formula: C6H5BrFN

Example 20i 3-Bromo-5-methylpicolinonitrile Potassium cyanide (5.76 g, 88.42 mmol) was added to a solution of 3-bromo-2-fluoro-5-methylpyridine (14 g, 73.68 mmol) in DMSO (75 mL) at rt. The resulting mixture was stirred at 110 C. for 1 h. More potassium cyanide (1.5 g, 23.03 mmol) was added and stirring continued for 20 min. Then the temperature was lowered to 80 C. and the mixture stirred over night. When cooled to rt, the mixture was poured into water (200 mL) and extracted with DCM (3*100 mL). The combined organics were washed with water (100 mL) then poured into a phase separator. The organic phase was collected, silica was added and the mixture was concentrated until a free flowing powder was obtained. The residue was purified on a silica gel column eluted with 0-50% EtOAc in heptane to afford 6.92 g (48% yield) of the title compound: 1H NMR (400 MHz, DMSO-d6) delta ppm 8.57-8.68 (m, 1H) 8.21-8.34 (m, 1H) 2.40 (s, 3 H); MS (CI) m/z 197, 199 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17282-01-8, 3-Bromo-2-fluoro-5-picoline, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; US2010/125081; (2010); 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.18368-73-5, name is 3-Methyl-2-nitropyridine, molecular formula is C6H6N2O2, molecular weight is 138.12, as common compound, the synthetic route is as follows.Computed Properties of C6H6N2O2

3-(Bromomethyl)-2-nitropyridine (3); A solution of 3-methyl-2-nitropyridine (2) (12.4 g, 90.0 mmol), NBS (16.0 g, 90.4 mmol) and AIBN (0.5 g, 3.0 mmol) in 0014 (50 mL) was refluxed overnight. TLC (Eluant: 20:1 petroleum ether/EtOAc) showed that most of the starting material had been consumed. The precipitate was filtered off and the filtrate was concentrated under reduced pressure to give a residue (12.6 g), which was used in the next step without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-73-5, 3-Methyl-2-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US2010/324043; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 20970-75-6 , The common heterocyclic compound, 20970-75-6, name is 2-Cyano-3-methylpyridine, molecular formula is C7H6N2, 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.

In a 40mL reaction bottle,Add 29.3mg (0.08mmol, 0.01eq.) In sequenceAllyl palladium chloride dimer, 92.6mg (0.16mmol, 0.02eq.)4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, 10.1mL1,4-dioxane, 1.38g (8mmol, 1.0eq.)2-Bromo-3-methylpyridine, 1.69g (4mmol, 0.5eq.)Potassium ferrocyanide trihydrate and 5.1mL water, adjust and control the temperature of the reaction liquid 95-105 , stirring for 18 hours;After the reaction,Add aqueous sodium hydroxide solution [0.38g (9.6mmol, 1.2eq.)Sodium hydroxide dissolved in 5.1mL water],Adjust and control the temperature of the reaction liquid 35-45 , stirring for 3 hours,Adjust the pH to 7-8 with 6M hydrochloric acid aqueous solution, and concentrate by distillation under reduced pressure at 50 C.Get a yellow-green solid,Column chromatography (200-300 mesh silica gel) separated 1.02g of light yellow solid,The yield was 93.6%. Analysis conditions are the same as in Example 1

The synthetic route of 20970-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai He Quan Pharmaceutical Co., Ltd.; Wang Xiaowei; Yao Lianbin; Zhu Jingyang; Fu Xiaoyong; Chen Minzhang; (6 pag.)CN110922285; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 73583-41-2, 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 73583-41-2, name is 4-Bromo-3-chloropyridine. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 01-51 Preparation of 3-[(3-chloropyridin-4-yl)amino]-2-methylcyclohex-2-en-l-one (01-51): 3- amino-2-methylcyclohex-2-enone (500 mg, 4 mmol), 4-bromo-3-chloropyridine (950 mg, 5 mmol), palladium acetate (90 mg, 0.4 mmol), BINAP (197 mg, 0.8 mmol), cesium carbonate (2.6 g, 8 mmol) and toluene (10 mL) were combined in a sealed flask and heated at 100C, for 18 h. At rt, the mixture was filtered and the filtrate was diluted with EtOAc (30 mL), washed with brine (3 x 10 mL), dried with Na2S04. The crude was purified by HPLC to afford the title compound (140 mg, 15% yield, white microcrystal, mp = 135-138C). 1H NMR (D6-DMSO) delta 1.46 (s, 3H), 1.83-1.88 (m, 2H), 2.31 (t, J= 6.7 Hz, 2H), 2.53-2.57 (m, 2H), 6.84 (d, J= 6.1 Hz, 1H), 8.06 (s, 1H), 8.29 (d, J= 6.1 Hz, 1H), 8.48 (s, 1H). 13C NMR (D6-DMSO) delta 10.9, 20.6, 28.7, 36.7, 115.7, 117.1, 121.2, 144.7, 148.3, 148.3, 149.2, 154.4, 197.0. LCMS t = 1.9 min, m/z Calcd for Ci2Hi4ClN20; Ci2Hi3ClN2NaO 237.080; 259.061 [M+H]+; [2M+H]+, Found 237.080; 259.180.

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 73583-41-2, 4-Bromo-3-chloropyridine.

Reference:
Patent; ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI; ZHOU, Ming-Ming; OHLMEYER, Michael; VINCEK, Adam; ZAWARE, Nilesh; WO2015/31824; (2015); 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. 120739-77-7, name is N-((6-Chloropyridin-3-yl)methyl)ethanamine. A new synthetic method of this compound is introduced below., name: N-((6-Chloropyridin-3-yl)methyl)ethanamine

Synthesis Example 3 2-chloro-5-[N-trifluoroacetyl-N-ethyl]aminomethylpyridine (Compound 21) A solution of 140 mg (0.67 mmol) of trifluoroacetic anhydride dissolved in 5 mL of anhydrous dichloromethane was added dropwise under ice cooling to a solution of 120 mg (0.70 mmol) of ethyl-(2-chloro-5-pyridylmethyl)amine synthesized by the method described in U.S. Patent Application Publication No. 2009306041 and 101 mg (1 mmol) of triethylamine dissolved in 5 mL of anhydrous dichloromethane. Following dropwise addition, the system was stirred overnight at room temperature, then the reaction mixture was washed with, in order, ice-cooled 1% aqueous sodium hydroxide, water, 1% hydrochloric acid, then water, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, giving 107 mg the target compound (yield, 78%).

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, 120739-77-7, N-((6-Chloropyridin-3-yl)methyl)ethanamine.

Reference:
Patent; MEIJI SEIKA PHARMA CO., LTD.; KAGABU, Shinzo; MITOMI, Masaaki; KITSUDA, Shigeki; HORIKOSHI, Ryo; NOMURA, Masahiro; ONOZAKI, Yasumichi; US2013/150414; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1221171-70-5, 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. 1221171-70-5, name is 2-Chloro-6-(trifluoromethoxy)pyridine. A new synthetic method of this compound is introduced below.

2-Chloro-5-iodo-6-trifluoromethoxy pyridine (41); At 0 0C, diisopropylamine (2.2 g, 3.1 mL, 22.2 mmol, 1.1 eq) was added dropwise to a solution of butyllithium (1.56 M in hexane, 14.2 mL, 22.2 mmol, 1.1 eq) in THF (35 mL). At -78 0C, a solution of 2-chloro-6-trifluoromethoxypyridine (2, 4.0 g, 20.2 mmol,1 eq) in THF (10 mL) was added dropwise followed after 2 h by a solution of iodide (5.7 g, 22.2 mmol, 1.1 eq) in THF (10 mL). The reaction mixture was allowed to reach 25 0C before being treated with a saturated aqueous solution of sodium sulfite (30 mL) and extracted with dichloromethane (3 x 20 mL). The combined organic layers were dried over sodium sulfate before being evaporated. The crude dark oil was distilled under vacuum (b.p. 103-106 0C / 16 mbar) to afford pure 2-chloro-5-iodo-6- trifluoromethoxypyridine (41, 5.1 g, 15.7 mmol, 78%) as colorless needles; m.p. 33-350C.1H NMR (CDCl3, 300 MHz): delta = 8.11 (d, J = 8.1 Hz, 1 H), 7.03 (d, J= 8.1 Hz, I H). – 19F NMR (CDCl3, 282 MHz): delta = -57.1 – 13C NMR (CDCl3, 75 MHz): delta = 154.9, 151.7, 148.8, 142.0, 123.3, 120.4 (q, J = 264 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1221171-70-5, 2-Chloro-6-(trifluoromethoxy)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1256789-09-9, 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. 1256789-09-9, name is Methyl 6-chloro-2,4-dimethylnicotinate. A new synthetic method of this compound is introduced below.

a) Synthesis of 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylesterTo a solution of 710 mg, (3.6 mmol) 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester in CCI4 (16 ml) were added 688 mg (3.90 mmol) N-bromosuccinimide, 59 mg (0.36 mmol) AIBN and 210 muIota (3.72 mmol) acetic acid . The reaction mixture was irradiated with a 200W Wolfram lamp at 60 C for 24 h. The mixture was then filtered through celite, washed with CCI4 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue a mixture of 6-chloro-2,4-dimethyl-pyridine-3-carboxylic acid methylester, 4-(bromomethyl)-6- chloro-2-methyl-pyridine-3-carboxylic acid methylester and 2-(bromomethyl)-6-chloro-4- methyl-pyridine-3-carboxylic acid methylester was obtained. This mixture was dissolved in dioxane (10 ml) and added at 0 C to a solution prepared by dissolving 594 mg (25.8 mmol) sodium in MeOH (11 ml) at 0 C. This reaction mixture was stirred at RT for 3 h. Then the reaction solution was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. After CC (hexane/EtOAc 97:3) of the residue again a mixture of 6-chloro-4-(methoxymethyl)-2-methyl- pyridine-3-carboxylic acid methylester and 6-chloro-2-(methoxymethyl)-4-methyl-pyridine-3- carboxylic acid methylester was obtained. This material was dissolved in NMP (7.8 ml) and 860 muIota (9.85 mmol) morpholine and 1.36 g (9.85 mmol) K2C03 were added followed by heating at 100 C for 5 h. Then the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 9:1) provided 90 mg (0.32 mmol, 9%) 2-(methoxymethyl)-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid methylester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1256789-09-9, Methyl 6-chloro-2,4-dimethylnicotinate, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; KUeHNERT, Sven; BAHRENBERG, Gregor; KLESS, Achim; SCHROeDER, Wolfgang; LUCAS, Simon; WO2012/52167; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem