Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 823-61-0, 3,6-Dimethyl-2-pyridinamine, 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, Formula: C7H10N2, blongs to pyridine-derivatives compound. Formula: C7H10N2

2-Chloromethyl-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine To a solution of 3,6-Dimethyl-2-pyridinamine (2.00 g, 16.4 mmol) in 50 mL of DCM was added dropwise a solution of hydroxylamine-2,4,6-Trimethyl-benzenesulfonate (4.22 g, 19.6 mmol) in 50 mL of CH2Cl2 at 0 C., and the mixture was stirred and allowed to warm to room temperature. The solvents were evaporated and the residue dissolved in 80 mL of MeOH then treated with DBU (3.43 mL, 22.9 mmol) and the solution stirred for 5 mins. After chloroacetic acid methyl ester (1.44 mL, 16.4 mmol) was added, the resultant mixture was stirred at room temperature for 48 h. After being concentrated under reduce pressure, the residue was diluted with water (100 mL) and extracted with EtOAc (3*100 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc=2/1) to give 2.65 g of 2-Chloromethyl-5,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine in 82% yield. LC-MS (MH+): m/z=195.9, tR (minutes)=1.14

At the same time, in my other blogs, there are other synthetic methods of this type of compound,823-61-0, 3,6-Dimethyl-2-pyridinamine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; US2012/129836; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 39658-41-8, 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. 39658-41-8, name is Ethyl 6-aminonicotinate, molecular formula is C8H10N2O2, 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 stirred solution of lithium aluminium hydride (183 mg, 4.83 mmol) in tetrahydrofuran was slowly added solution of ethyl 6-aminonicotinate (200 mg, 1.21 mmol) in tetrahydrofuran at 0 C under nitrogen atmosphere. The reaction mixture was stirred at 0 C for 30 minutes then at room temperature for 3 h. The mixture was quenched at 0 C with 1 HCI until pH is 3 then basified with sodium carbonate solution until pH is 7. Then the mixture was filtered using celite to remove LAH residue and it was dissolved in ethyl acetate and washed with saturated sodium carbonate solution. The organic layer was dried (magnesium sulphate) and filtered. The filtrate was removed in vacuo. The crude condition of (6- aminopyridin-3-yl)methanol (55 mg, crude) was obtained in 75 % yield.

According to the analysis of related databases, 39658-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; WO2013/13815; (2013); 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. 72716-86-0, name is 2-Methoxyisonicotinonitrile. A new synthetic method of this compound is introduced below., category: pyridine-derivatives

Example 2; Synthesis of l-(2-methoxy-pyridin-4-yl)-propan-l-one; A stirred suspension of 25.44 g of 2-methoxy-isonicotinonitrile as obtained in Example 1 (189.7 rnmol) in 380 niL TBME was cooled to 0 C and 114 mL ethyl magnesium chloride in THF(2.0 M, 228.0 mmol, 1.20 eq) were added within 45 min. Stirring was continued at O0 C. After 3 h 40 min, additional 5 mL ethyl magnesium chloride in THF(2.0 M, 10.0 mmol, 0.05 eq) were added at 0 C. The reaction was monitored by HPLC. After 4.5 h (< 3 % area 2-methoxy-isonicotinonitrile), the reaction was quenched at 0 C by addition of 300 mL water. The resulting suspension was stirred for 16 h at room temperature and was then diluted with 200 mL toluene. The aqueous phase was extracted with 400 mL toluene and the combined organic phases were washed with 500 mL saturated aqueous NH4Cl and 500 mL brine, dried over 50 g Na2SO4 (30 min) and filtered. The filter cake was washed with 100 mL toluene. After evaporation of solvent in a rotary evaporator (40C/10 mbar), the title compound (28.64 g, 91 % by weight) was obtained as an orange solid. M^: 38C;1R NMR (300 MHz, CDCl3): delta 8.30 (d, IH5 J= 5.3 Hz), 7.30 (dd, IH5 J= 5.3 Hz5 J= 1.3), 7.18 (br. s, IH), 3.98 (s, 3H)5 2.96 (q, 2H, J= 7.2 Hz), 1.22 (t, 3H, J- 7.2 Hz) ppm 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, 72716-86-0, 2-Methoxyisonicotinonitrile. Reference:
Patent; SOCIETE DE CONSEILS DE RECHERCHES ET D’APPLICATIONS SCIENTIFIQUE (S.C.R.A.S.); WO2006/33011; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 150114-71-9, 4-Amino-3,6-dichloropicolinic 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, HPLC of Formula: C6H4Cl2N2O2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H4Cl2N2O2

1. Preparation of Methyl 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylate A solution of 4-amino-3,6-dichloropyridine-2-carboxylic acid (1100 g, 5.31 mol), 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octanebis(tetrafluoroborate) (2100 g, 5.93 mol) in water (6000 mL) was warmed to 65 C. for six hours. After cooling to ambient temperature, the reaction mixture was stirred an additional 18 hours. The solution was concentrated and the resulting solid washed with 6 N hydrochloric acid (5*1000 mL) and dried to give 4-amino-3,6-dichloro-5-fluoropyridine-2-carboxylic acid (757 g, 3.53 mol. 58% purity). This crude material was added to methanol (3000 mL) which had been saturated with anhydrous hydrogen chloride and the reaction mixture was warmed to 45 C. for 2 hours. The solution was added with vigorous stirring to ice water (4000 mL) and the resulting solid collected.

The synthetic route of 150114-71-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Balko, Terry William; Buysse, Ann Marie; Fields, Stephen Craig; Irvine, Nicholas Martin; Lo, William Chi-Leung; Lowe, Christian Thomas; Richburg, John Sanders; Schmitzer, Paul Richard; US2004/198608; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1206968-92-4, (5-Bromo-3-fluoropyridin-2-yl)methanol, 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, SDS of cas: 1206968-92-4, blongs to pyridine-derivatives compound. SDS of cas: 1206968-92-4

A microwave vial was charged, in succession, with (5 -bromo-3 -fluoropyridin-2- yl)methanol (100 mg, 0.485 mmol), 7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)quinoline (124 mg, 0.485 mmol), 1 , -bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (35 mg, 0.043 mmol), 1,4-dioxane (3 mL), and 2M aq. potassium carbonate (1.5 mL). The vial was capped, purged with nitrogen, and stirred at 100 C. After 30 minutes, the reaction mixture was cooled to room temperature, allowing the organic phase to separate from the aqueous. The organic layer was removed and filtered through a plug of Celite and sodium sulfate. The plug was washed with dioxane (10 mL). The organic filtrate was concentrated in vacuo. Purification via flash chromatography (0-10% methanol/dichloromethane) afforded the title compound (150 mg, 103%). Although the recovered weight exceeded the theoretical yield, the compound was used without further purification. MS(ES)+ m/e 255.2 [M+H]+.

The synthetic route of 1206968-92-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; ADAMS, Nicholas, David; CHAUDHARI, Amita, M.; KIESOW, Terence, John; McSHERRY, Allison, K.; MOORE, Michael, Lee; PARRISH, Cynthia, Ann; REIF, Alexander, Joseph; RIDGERS, Lance, Howard; WO2014/8223; (2014); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 23056-47-5, 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 23056-47-5 as follows.

2-Bromo-4-methyl-5-nitropyridine (2.5g, 11.58mmol) was dissolved in concentrated sulfuric acid (25mL), cooled to ice bath 0C, chromium trioxide (3.88g, 38.8mmol) was added. It was slowly warmed to room temperature and stirred overnight. The reaction mixture was poured into ice water (75 mL), stirred for 10 minutes and suction filtered to give a white solid (2.5g, yield: 87.8%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,23056-47-5, its application will become more common.

Reference:
Patent; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; Yang Xiaoju; (118 pag.)CN109575016; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 709652-82-4, 2-Amino-5-bromonicotinonitrile, 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, Safety of 2-Amino-5-bromonicotinonitrile, blongs to pyridine-derivatives compound. Safety of 2-Amino-5-bromonicotinonitrile

Step-2 [0069] To a stirred solution of compound 2 (4.6 g) in HCl (48.4 mL) was added sodium nitrite (5.3 mL) dropwise at -5 C. The reaction mixture was stirred at room temperature for 2 h. The resulting solids were collected by filtration and dried in vacuum to give compound 3 (4.4 g, 88%).

The synthetic route of 709652-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rangarajan, Radha; Kumar, Rajinder; Prabhakar, BV; Chandrasekhar, P; Mallikarjuna, P; Banerjee, Ankita; US2014/249170; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 125903-77-7, Adding some certain compound to certain chemical reactions, such as: 125903-77-7, name is 3-Methylpicolinimidamide hydrochloride,molecular formula is C7H10ClN3, 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 125903-77-7.

A mixture of 1-(4-methylsulfonylphenyl)piperidin-4-one (100 mg, 0.39 mmol) andDMFDMA (1 mL) in acetonitrile (8 mL) was heated with stuffing at 90 C for 2 hrs. Theresulting mixture was concentrated in vacuo and the residue was dissolved in EtOH (lOmL). To the solution was added 3-methylpyridine-2-carboxamidine hydrochloride (53 mg, 0.39 mmol) and potassium carbonate (88 rng, 064 mmoi) successively. After being heated at 90 C overnight, the reaction mixture was cooled to rt, diluted with water (20 mL) and extracted with EA (20 mL)for three times. The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by prepHPLC to give 2-(3-methyl- 2-pyridyl)-6-(4-methylsulfonylphenyl)-7 ,8-dihydro-5H-pyrido [4,3-d]pyrimidine (20 mg). ?H NMR (400MHz, CDC13): oe 8.75 (s, 1H), 8.64 (dd, 1H), 7.87(d, 2H), 7.67 (d, 1H), 7.34 – 7.28 (m, 1H), 7.06 (d, 2H), 4.65 (s, 2H), 3.88 (t, 2H), 3.29 (t, 2H), 3.05 (s, 3H), 2.54 (s, 3H). MS obsd.(ESIj [(M+H)]: 381.

According to the analysis of related databases, 125903-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1122-43-6, 2,6-Dimethyl-3-hydroxypyridine, 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, 1122-43-6, blongs to pyridine-derivatives compound. Product Details of 1122-43-6

Step A: 2,6-Dimethylpyridin-3-ol (1.0 g, 8.1 mmol) was dissolved in aqueous NaOH (4.05 mL, 2 M, 8.1 mmol). To the solution was added iodine (2.62 g, 10.3 mmol) at room temperature. The mixture was stirred at 50 C. for 2 h, then neutralized (pH ?7) with aqueous HCl (2 N). Excess reagent was quenched with sodium thiosulfate, then the solvent was removed under vacuum. The residue was suspended in 10% MeOH in CH2Cl2 (100 mL) and filtered. The filtrate was concentrated to give 4-iodo-2,6-dimethylpyridin-3-ol (0.96 g, 50%). MS m/z 250.0 [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,1122-43-6, its application will become more common.

Reference:
Patent; PTC Therapeutics, Inc.; F. Hoffmann-La Roche AG; Woll, Matthew G.; Chen, Guangming; Choi, Soongyu; Dakka, Amal; Huang, Song; Karp, Gary Mitchell; Lee, Chang-Sun; Li, Chunshi; Narasimhan, Jana; Naryshkin, Nikolai; Paushkin, Sergey; Qi, Hongyan; Turpoff, Anthony A.; Weetall, Marla L.; Welch, Ellen; Yang, Tianle; Zhang, Nanjing; Zhang, Xiaoyan; Zhao, Xin; Pinard, Emmanuel; Ratni, Hasane; (317 pag.)US9617268; (2017); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 403-45-2 ,Some common heterocyclic compound, 403-45-2, molecular formula is C6H4FNO2, 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.

Methyl 6-fluoronicotinate. To a solution of 6-fluoronicotinic acid (255 mg, 1.32 mmol) in methanol (5 mL) at room temperature was added (trimethylsilyl)diazomethane (4.0 mL, 2 M in diethyl ether, 8.0 mmol). The reaction mixture was stirred at room temperature for 30 min and concentrated. Methyl 6- fluoronicotinate (129 mg, 47%) was used without further purification: 1H NMR (600 MHz, DMSOd6) delta 8.79 (d, J = 2.6 Hz, IH), 8.47 (td, J = 7.9, 2.6 Hz, IH), 7.35 (ddd, J = 8.5, 2.6, 0.6 Hz, IH), 3.88 (s, 3H); ESIMS calcd 156.0 (M+ + H), found 156.1 (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,403-45-2, its application will become more common.

Reference:
Patent; MERCK & CO., INC.; ATON PHARMA, INC.; WO2007/2248; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem