Tag: M.W:100-200

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

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

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.709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.Computed Properties of C6H4BrN3

To a solution of 2-amino-5-bromonicotinonitrile (1.4 equiv.) in toluene and ethanol (2.5:1) was added N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)-3-(trifluoromethyl)benzamide (1.0 equiv.), Pd(PPh3)4 (0.1 equiv.) and aqueous potassium carbonate (3M, 3.0 equiv.). The reaction was heated in the microwave at 120 C for 40 min. The organic layer was separated and concentrated to dryness under vacuo. The residue was dissolved in DMSO and purified via reverse phase HPLC. The pure fractions were lyophilized to give N-(3-(6-amino-5-cyanopyridin-3-yl)-4-methylphenyl)-3- (trifluoromethyl)benzamide as the TFA salt in 48% yield. 1H NMR (400 MHz, DMSOd6) G 10.45 (s, 1H), 8.30 (s, 1H), 8.25 (d, J=2.0, 1H), 8.23 (d, J=2.0, 1H), 7.97 (d, J=8.0, 1H), 7.95 (d, J=4.0, 1H), 7.79 (t, J=8.0, 1H), 7.72 (dd, J=8.0, 2.0, 1H), 7.61 (d, J=4.0, 1H), 7.30 (d, J=12.0, 1H), 2.23 (s, 3H). LCMS (m/z) (M+H) = 397.1, Rt = 0.91 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,709652-82-4, 2-Amino-5-bromonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (2016); 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.1254473-66-9, name is 1-(3,5-Dichloropyridin-4-yl)ethanol, molecular formula is C7H7Cl2NO, molecular weight is 192.04, as common compound, the synthetic route is as follows.Computed Properties of C7H7Cl2NO

(30eq) was added to 30 ml of anhydrous THF and 327 mg (3.0 eq) of 60% NaH was added. After 30 min of activation, 400 mg of the starting material 17 was added and the reaction was complete after 12 hours of refluxing. Water and acetic acid The combined organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was dried to give brown oil 18 (420 mg) in 57.3% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1254473-66-9, 1-(3,5-Dichloropyridin-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; SICHUAN BAILI PHARMACEUTICAL CO LTD; WU, YONG; ZHU, YI; HAI, LI; WANG, YIXI; LI, JIE; (23 pag.)CN105906621; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89809-63-2, 5-Methoxypicolinonitrile, 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, 89809-63-2, blongs to pyridine-derivatives compound. Safety of 5-Methoxypicolinonitrile

General procedure: To a solution of diisopropylamine (170 muL, 1.2 eq.) in dry THF (2 mL) in a flame dried round bottom flask under argon at 0 C was added n-butyllithium (690 muL, 1.6 M in hexanes, 1.1 eq.), and the reaction mixture was stirred at this temperature for 15 minutes. It was then cooled to -78 C and a solution of ketone (1) (1 mmol) in THF (2 mL) slowly added. Stirring at -78 C was continued for a further 30 minutes and methyl chlorosulfate (100 muL, 1.1 eq.) was then added. After stirring at -78 C for 30 minutes, the reaction was quenched with an aqueous saturated ammonium chloride solution (5 mL). The mixture was then extracted with dichloromethane (3 x 5 mL), the combined organic phases were dried with anhydrous magnesium sulfate and the solvent evaporated under vacuum affording the desired alpha-chloroketone 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89809-63-2, its application will become more common.

Reference:
Article; Silva, Saul; Maycock, Christopher D.; Tetrahedron Letters; vol. 59; 13; (2018); p. 1233 – 1238;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem