Tag: M.W:100-200

Reference of 105166-53-8 , The common heterocyclic compound, 105166-53-8, name is [2,2′-Bipyridin]-3-amine, molecular formula is C10H9N3, 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.

General procedure: Trifluoroacetic acid (0.75 mL, 0.009 mol) was added to a cooled (0 C) solution (4.5 mL CH2Cl2) of3-amino-2,2?-bipyridine (0.513 g, 0.003 mol), followed by isoamyl nitrite (0.61 mL, 0.004 mol). After 1 h,the diazonium salt of 3-amino-2,2?-bipyridine was precipitated out by cooling the reaction mixtureto -78 C, followed by the addition of diethyl ether (30 mL). The precipitate was filtered. A sample(2 mmol; 0.27 g) of indol-2-one was dissolved in dilute potassium hydroxide solution (15 mL) andcooled in a saltice bath and then cold diazonium solution was added to this cooled solution portionwise by stirring. The solution was further stirred at 0-5 C for 1 h. The pH of the reaction mixturewas maintained at 4-6 by the addition of solid sodium acetate in portions. The mixture was stirredfor 24 h at room temperature. The resulting solid was filtered, washed with cold water, and air-dried.Crystallization from ethanol gave yellow crystalline.(Z)-3-(2-(2,2?-bipyridin-3-yl)hydrazono)indolin-2-one (3), yellow solid (328 mg, 52%): 1H-NMR (600 MHz,DMSO): delta15.70 (s, 1H), 10.89 (s, 1H), 8.80 (d, J = 4.0 Hz, 1H), 8.50 (d, J = 8.1 Hz, 1H), 8.45 (dd, J = 8.4,1.3 Hz, 1H), 8.37 (dd, J = 4.3, 1.4 Hz, 1H), 8.04-7.98 (m, 1H), 7.62 (d, J = 7.4 Hz, 1H), 7.54-7.46 (m, 1H),7.25 (dd, J = 7.6, 6.7 Hz, 1H), 7.04 (t, J = 7.2 Hz, 1H), 6.92 (d, J = 7.7 Hz, 1H). 13C-NMR (151 MHz,DMSO) delta161.83, 156.74, 147.04, 142.28, 140.39, 139.61, 137.59, 137.13, 130.36, 128.95, 125.16, 123.13,121.90, 121.74, 121.61, 121.27, 119.08, 110.29. Elem. anal. calcd. for C18H13N5O, C 68.56, H 4.16, N 22.21.Found: C 68.48, H 4.09, N 21.88. IR (ATR) nu/cm-1: 3180, 3047, 1693, 1464, 1164, 798. m.p: 238-240 C.

The synthetic route of 105166-53-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; ?andrik, Robert; Tisovsky, Pavol; Csicsai, Klaudia; Donovalova, Jana; Gaplovsky, Martin; Sokolik, Robert; Filo, Juraj; Gaplovsky, Anton; Molecules; vol. 24; 14; (2019);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1122-61-8, name is 4-Nitropyridine, molecular formula is C5H4N2O2, 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. COA of Formula: C5H4N2O2

Example 15 4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25 C. After completion of the addition, the resulting mixture was at 25 C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

With the rapid development of chemical substances, we look forward to future research findings about 1122-61-8.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5648496; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 65515-39-1, 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. 65515-39-1, name is 2-Methoxy-4,6-dimethylnicotinonitrile. A new synthetic method of this compound is introduced below.

(a) 2-methoxy-6-methyl-4-(pent-4-en-l-yl)nicotinonitrile To a solution of 2-methoxy-4,6-dimethylnicotinonitrile (1.115 g, 6.87 mmol) in THF (20 mL) was added LiHMDS (1 M in toluene, 7.22 mL, 7.22 mmol) at 0 C dropwise via syringe over 10 min, and the reaction was stirred at this temperature for 1 h. 4- Bromobut-l-ene (0.733 mL, 7.22 mmol) was added dropwise via syringe and the mixture was stirred from 0 C to room temperature overnight. The reaction was poured into saturated aqueous ammonium chloride (50 mL) and extracted with EtOAc (3 x 75 mL). The combined organics were dried over Na2S04, filtered, concentrated, and the residue purified by flash chromatography (0-20% EtOAc in hexanes, 40-g column, product fractions pooled and recolumned 0-10% EtOAc in hexanes, 40-g column) to afford 2- methoxy-6-methyl-4-(pent-4-en-l-yl)nicotinonitrile (619 mg, 42%) as a colorless oil. LC- MS(ES) m/z = 217 [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,65515-39-1, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; KNIGHT, Steven David; LAFRANCE, Louis Vincent III; MCNULTY, Kenneth C.; ROMERIL, Stuart Paul; SEEFELD, Mark Andrew; WO2014/195919; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 59944-76-2, name is Thieno[2,3-b]pyridine-2-carboxylic acid, molecular formula is C8H5NO2S, 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. Recommanded Product: Thieno[2,3-b]pyridine-2-carboxylic acid

Coupling: Example 13 is obtained as a white salt (9% yield) using acid C102 according to Method A with non-critical changes. HRMS (FAB) calculated for C15H17N3OS+H: 288.1170, found 288.1175 (M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 59944-76-2.

Reference:
Patent; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Groppi JR., Vincent E.; US2003/45540; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 66909-38-4, 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 66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine. This compound has unique chemical properties. The synthetic route is as follows.

Compound 6-chloro-4-methylpyridin-3-amine 6a (6.75 g, 47.3 mmol), N-iodosuccinimide (12.95 g, 57.6 mmol), and N,N-dimethylformamide (100 mL) were mixed at 0C and stirred at room temperature for 15 hrs. Next, water (100 ml) was added, and the mixture was extracted with ethyl acetate (150 mL*3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered to remove the desiccant, and concentrated to remove solvent under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate= 10/1) to give a target product 6-chloro-2-iodo-4-methylpyridin-3-amine 6b (6.5 g, yellow solid), yield: 47%. MS m/z (ESI):269[M+1]

According to the analysis of related databases, 66909-38-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing InnoCare Pharma Tech Co., Ltd.; CHEN, Xiangyang; PANG, Yucheng; (44 pag.)EP3409672; (2018); 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.10273-89-9, name is 2-(o-tolyl)pyridine, molecular formula is C12H11N, molecular weight is 169.22, as common compound, the synthetic route is as follows.Product Details of 10273-89-9

General procedure: Unless otherwise stated, in an Argon filled glove-box a crimp-cap microwave vial equipped with a magnetic stirring bar was charged with the appropriate cyclometalated Ru(ll)-catalyst (like Ru1-Ru46, from 3 mol % to 10 mol %), KOAc (5.9 mg, 0.06 mmol, 30 mol %), K2CO3 (2.0 – 4.0 equiv.), the appropriate DG-containing arene (like N1-N12, 0.20 mmol, 1.0 equiv.), the appropriate (hetero)aryl (pseudo)halide (like X1-X42, 0.2 mmol, 1.0 equiv) and /V-methyl-2- pyrrolidone (NMP) (200 pL, 1 M). The vial was capped and stirred at 35 C for 24 hours. Upon completion, the crude mixture was loaded on a silica gel column and purified by flash chromatography.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,10273-89-9, 2-(o-tolyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; THE UNIVERSITY OF MANCHESTER; LARROSA, Igor; SIMONETTI, Marco; CANNAS, Diego Maria; (94 pag.)WO2019/215426; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 936841-69-9 ,Some common heterocyclic compound, 936841-69-9, molecular formula is C7H3F3N2, 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.

[0209] A mixture of 4-(trifluoromethyl)picolinonitrile (840mg, 4.88 mmol) and 10%Pd/C (168 mg, 0.16 mmol) was stirred under hydrogen (balloon) in MeOH (10 mL) at ambient temperature for overnight. The reaction mixture was filtered through Celite and concentrated to afford (4- (trifluorom ethyl )pyridin-2-yl)methanamine as an oil. LC/MS = 177 [M+l].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,936841-69-9, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUANG, Rongze; TING, Pauline; ALI, Amjad; WU, Heping; BERLIN, Michael; STAMFORD, Andrew; WANG, Hongwu; ZHOU, Gang; KIM, David; DENG, Qiaolin; LIM, Yeon-Hee; YU, Younong; (201 pag.)WO2016/81290; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 145255-19-2, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 145255-19-2 as follows.

[1144] 40 mg (0.098 mmol) of 2-[4-(5-chioro-2-cyano- phenyl)-5-methoxy-2-oxopyridin-i (2H)-yl] -3-(i ,3-oxazol- 2-yl)propanoic acid (racemate) and 20mg (0.147 mmol, 1.5 eq.) of 5-aminopyridine-2-carboxamide were initially charged in 0.8 ml of pyridine, 93 j±1 (0.392 mmol, 50% in ethyl acetate, 4.0 eq.) of T3P were added and the mixture was stirred at 50 C. for 2 h. The reaction mixture was cooled, 6 ml of saturated aqueous sodium hydrogencarbonate solution were added and the mixture was stirred for 15 mm. The crystals formed were filtered oil with suction and washed with water, 500 j±1 of isopropanol and then pentane. The residue was dried under high vacuum. Yield: 29 mg (57% of theory).11145] LCMS [Method 1]: R=0.79 mm; MS (ESIpos):mlz=5 19 (M+H), j1146] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=i0.91(s, 1H), 8.84 (d, 1H), 8.20 (dd, 1H), 8.07-7.95 (m, 4H), 7.73 (dd, 1H), 7.68 (d, 1H), 7.52 (s, 2H), 7.12 (s, 1H), 6.51 (s, 1H), 6.00 (t, 1H), 3.78 (d, 2H), 3.64 (s, 3H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,145255-19-2, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ROeHRIG, Susanne; JIMENEZ-NUNEZ, Eloisa; SCHLEMMER, Karl-Heinz; TERSTEEGEN, Adrian; TELLER, Henrik; HILLISCH, Alexander; HEITMEIER, Stefan; SCHMIDT, Martina Victoria; ACKERSTAFF, Jens; STAMPFUss, Jan; (87 pag.)US2017/291892; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 184416-83-9, name is 2,3-Dichloropyridin-4-amine. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

A solution of 2,3-dichloropyridin-4-amine (900 mg, 5.521 mmol), (Boc)2O (3012.52 mg, 13.803 mmol), Et3N (2230.61 mg, 22.085 mmol), DMAP (67.36 mg. 0.552 mmol) in CH2Cl2 was stirred at rt for 12 h. The mixture was diluted with water (100 mL) and extracted with CHI-2Cl2 (100 mL*3). The organic layers were dried (MgSO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (eluent: petrol ether/EtOAc=100:0 to 70:30). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford 4,4-tert-butyl carbamate-2,3-dichloropyridin-4-amine, cpd 119a (1600 mg, 77.7% yield) as a white solid. LCMS (ESI) m/z M+1: 362.8.

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, 184416-83-9, 2,3-Dichloropyridin-4-amine.

Reference:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 52092-47-4, Adding some certain compound to certain chemical reactions, such as: 52092-47-4, name is 5-Chloro-2-nitropyridine,molecular formula is C5H3ClN2O2, 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 52092-47-4.

To a solution of 5-chloro-2-nitropyridine (3 g, 19 mmol) in EtOH (30 mL) was added saturated NH3.H2O (20 mL) ‘ the mixture was stirred under 50 psi at 150 C overnight. TLC showed that the reaction was complete. After the reaction mixture was cooled to r.t, the resulting solid was collected by filtration. The solid was washed with PE (100 mL) to give 0.7 g (yield: 26%) of 6-nitro-pyridin-3-ylamine as a yellow solid. MS: m/z 140.1 (M+H+).

According to the analysis of related databases, 52092-47-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; PINKERTON, Anthony, B.; DAHL, Russell; COSFORD, Nicholas, D.P.; MILLAN, Jose, Luis; WO2013/126608; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem