Month: April 2022

Reference of 167837-43-6, 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 167837-43-6, name is (E)-3-(6-Aminopyridin-3-yl)acrylic acid. This compound has unique chemical properties. The synthetic route is as follows.

EDC hydrochloride (118 mg, 0.62 mmol) was added to a solution of methyl- thieno [3,2-c] PYRIDINE-2-YLMETHYL-AMINE (100 mg, 0.56 mmol), (E)-3-(6-AMINO-PYRIDIN-3- yl) acrylic acid (101 mg, 0.62 mmol), HOBT H2O (83 mg, 0.62 mmol) and triethylamine (235 FL, 1.68 mmol) in anhydrous DMF (5 mL). The mixture was stirred at room temperature overnight then diluted with H20 (10 mL) and extracted with CH2C12 (3 x 50 mL). The combined organic fractions were dried over MGS04, filtered and evaporated to give a yellow residue which was subjected to flash chromatography on silica gel (10% MeOH : CH2C12) to yield the title compound (61. 0%).’H-NMR (300 MHz, CDC13) 6 9.04 (s, 1H), 8.45 (d, J= 5.3Hz, 1H), 8.26 (s, 1H), 7.76-7. 67 (m, 3H), 7.32 (d, J= 15. 0Hz, 1H), 6.76 (d, J= 15.2 Hz, 1H), 6.53 (d, J= 8.3 Hz, 1H), 4.95 (s, 2H), 4.76 (br s, 2H), 3.22 (s, 3H); MS (ES) m/e 325.1 (M+H) +.

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 167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic acid.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); 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

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

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

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

Synthetic Route of 1214328-96-7, 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 1214328-96-7, name is Methyl 3-bromo-6-chloropicolinate. This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 2 Synthesis of 3-bromo-4,6-dichloro-pyridine-2-carboxylic acid methyl ester.2.1 Preparation of 3-bromo-6-chloro-pyridine-2-carboxylic acid N-oxideUrea hydrogen peroxide (65.32 g, 347.2 mmol) was added portionwise to a solution of trifluoroacetic anhydride (145.8 g, 694.4 mmol, 96.5 mL) in dichloromethane (577 mL) at 0 C. 3-Bromo-6-chloro-pyridine-2-carboxylic acid methyl ester (27.18 g, 108.5 mmol) was added to the mixture portionwise and the reaction was stirred at room temperature for 19 h. The reaction was quenched by the addition of water, and the organic layer was washed with water and saturated aqueous K2C03. The organic layer was dried (MgS04) and concentrated in vacuo to give 3-bromo-6-chloro-pyridine-2-carboxylic acid N-oxide as a yellow oil.Characterising data for the compound are as follows: NMR (400 MHz, CD3OD) delta ppm 7.77-7.75 (m, 2H) and 4.01 (s, 3H).

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 1214328-96-7, Methyl 3-bromo-6-chloropicolinate.

Reference:
Patent; SYNGENTA LIMITED; WHITTINGHAM, William Guy; HACHISU, Shuji; ASPINALL, Mary, Bernadette; HOTSON, Matthew, Brian; WO2011/144891; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1030626-87-9 , The common heterocyclic compound, 1030626-87-9, name is 8-Bromo-5-chloro-[1,2,4]triazolo[1,5-a]pyridine, molecular formula is C6H3BrClN3, 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.

A.5 (5-Chloro-[l, 2, 4]triazolo[l, 5-a]pyridin-8-yl)-(4-morpholin-4-yl-phenyl)-amine[0332] A suspension of 8-bromo-5-chloro-[l,2,4]triazolo[l,5-a]pyridine (160 mg, 0.69 mmol),4-morpholin-4-yl-phenylamine (135 mg, 0.76 mmol), sodium-tert-butoxide (93 mg, 0.96 mmol), tris(dibenzylideneacetone)dipalladium (0) (13 mg, 13.76 mumol) and Xantphos (16 mg, 27.52 mumol) in dry toluene is heated at 90 0C in a sealed tube under a nitrogen atmosphere for 16 hours. The reaction mixture is evaporated to dryness and the residue partitioned between dichloromethane and 10 % aqueous citric acid. The organic phase is further washed with water (Ix) and brine (Ix), dried over magnesium sulfate, filtered and evaporated. The solid residue (207 mg) is purified by flash chromatography (silica gel, dichloromethane/methanol 97:3) affording the title compound (70 mg) as a solid.

The synthetic route of 1030626-87-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS N.V.; BURRITT, Andrew; WO2008/65198; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 195044-14-5, 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 195044-14-5, name is 2-Bromo-6-tert-butylpyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 58A[0972] 2-(benzylthio)-6-tert-butylpyridine[0973] To a solution of benzyl mercaptan (0.22 mL, 1.87 mmol) in anhydrous N,N- dimethylformamide (10 mL) was added a 1.0 M solution of potassium tert-butoxide in tetrahydrofuran (1.87 mL, 1.87 mmol) dropwise over 2 minutes. To the resulting suspension was added 2-bromo-6-tert-butylpyridine (0.20 g, 0.93 mmol), and the resulting mixture was stirred at 50 C for 16 hours. The cooled mixture was poured into water (50 mL) and extracted with ethyl acetate (50 mL), and the ethyl acetate layer was dried over Na2S04, filtered and concentrated in vacuo to give a crude product. Purification by column chromatography on silica gel using hexanes gave the titled compound. XH NMR (300 MHz, CDC13) delta ppm 1.35 (s, 9 H), 4.50 (s, 2 H), 6.93 – 7.03 (m, 2 H), 7.17 – 7.45 (m, 6 H); MS (APCI) m/z 258.3 (M+H)+.

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 195044-14-5, 2-Bromo-6-tert-butylpyridine.

Reference:
Patent; ABBVIE INC.; LI, Tao; PATEL, Sachin, V.; PERNER, Richard, J.; RANDOLPH, John, T.; SCHRIMPF, Michael, R.; WOLLER, Kevin, R.; XIA, Zhiren; ZHANG, Qingwei; WO2013/49174; (2013); 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

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