Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1659-31-0, Dipyridin-2-yl carbonate, 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, name: Dipyridin-2-yl carbonate, blongs to pyridine-derivatives compound. name: Dipyridin-2-yl carbonate

To a suspension of sodium hydride, 60% in mineral oil (0.817 g, 20.43 mmol) in THF (55 mL) was added 3-methyloxetan-3-ol (1.5 g, 17.03 mmol) at 0 C. After stirring 30 min, the solution was transferred to a solution of di(pyridin-2-yl) carbonate (3.68 g, 17.03 mmol) in THF (55 mL) through a cannula. The formed slurry was stirred at 0 C. for 30 min. The slurry was warmed to rt and stirred for 2 h. The reaction was diluted with EtOAc, washed with brine, dried over MgSO4, filtered, concentrated to give a residue that was purified by Biotage (5-40% EtOAc:Hex) to afford the desired product 3-methyloxetan-3-ylpyridin-2-yl carbonate (1.00 g, 28.1% yield) as an oil.1H NMR (400 MHz, CHLOROFORM-d) delta 8.52-8.35 (m, 1H), 7.84 (ddd, J=8.1, 7.3, 2.1 Hz, 1H), 7.31-7.27 (m, 1H), 7.15 (dt, J=8.1, 0.8 Hz, 1H), 4.97-4.85 (m, 2H), 4.54 (d, J=8.0 Hz, 2H), 1.86 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1659-31-0, Dipyridin-2-yl carbonate, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P.V.K. Suresh; Scola, Paul Michael; (403 pag.)US9527885; (2016); B2;,
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.147149-98-2, name is 4-Amino-2-(trifluoromethyl)pyridine, molecular formula is C6H5F3N2, molecular weight is 162.11, as common compound, the synthetic route is as follows.SDS of cas: 147149-98-2

To a solution of 2,4-dichloro-6-(4- (trifluoromethyl)pyrimidin-2-yl)-l,3,5-triazine (981 mg, 3.31 mmol) in THF (80 mL) was added 2-(trifluoromethyl)pyridin-4-amine (590 mg, 3.64 mmol) and NaHC03 (556 mg, 6.6 mmol). The mixture was stirred at refluxing for 18 hours. The mixture was concentrated and poured to water, extracted with ethyl acetate, dried over sodium sulphate, filtered and concentrated to give a residue, which was purified by Si02 chromatography to give 4-chloro-6-(4-trifluoromethyl- pyrimidin-2-yl)-[l,3,5]triazin-2-yl]-(2-trifluoromethyl-pyridin-4-yl)-amine. LCMS: m/z 422.2 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,147149-98-2, 4-Amino-2-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; TRAVINS, Jeremy; UTLEY, Luke; WO2015/6592; (2015); 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. 100-48-1, name is Isonicotinonitrile, molecular formula is C6H4N2, 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. Safety of Isonicotinonitrile

(d) 4-Pyridinecarboxamidine hydrochloride A solution of 4-pyridinecarbonitrile (370 g, 3.55 mol) and sodium methoxide (20.0 g, 0.37 mol) in methanol (1.71) was stirred at room temperature for 1.5 hours, then ammonium chloride (200 g, 3.7 mol) was added. The reaction mixture was stirred for 24 hours, the resulting solid was collected by filtration and the filtrate was evaporated to dryness. The two crops were combined and recrystallized from water to afford 394 g (70percent) of 4-pyridinecarboxamidine hydrochloride, m.p. 250°-252° C. (dec.).

With the rapid development of chemical substances, we look forward to future research findings about 100-48-1.

Reference:
Patent; Sterling Winthrop Inc.; US5294612; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 189089-90-5, 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. 189089-90-5, name is 1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid, molecular formula is C14H10N2O4S, 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.

General procedure: A mixture of substituted pyridine N-oxide 1 (1 eq),heteroaryl carboxylic acid 2 (2 eq), Pd(OAc)2 (10 mol %), pyridine (3 eq) and Ag2O (2.5 eq) in DMF: CH3CN (1:2, 6 mL) was stirredat 110 C for 12 h. The reaction mixture was filtered through celite pad, washed with ethyl acetate. The organic layer was washed withwater and brine, dried over sodium sulfate, and concentrated in vacuum. Crude product was purified by either CombiFlash Rf orGrace Instrument using Teledyne Isco RediSep Rf columns (Normal-phase-12 g) 2-4% methanol in dichloromethane mixture as thesolvent to get 3.

According to the analysis of related databases, 189089-90-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Suresh, Rajendran; Muthusubramanian, Shanmugam; Senthilkumaran, Rajendran; Synlett; vol. 25; 14; (2014); p. 2064 – 2066;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1008-91-9, 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. 1008-91-9, name is 1-(Pyridin-4-yl)piperazine. A new synthetic method of this compound is introduced below.

General procedure: A solution of AlMe3 in toluene (1.5 mol equiv., 2 M) was added to the methyl benzoate 16 or 17 (1.0 mmol) dissolved in toluene (3.5 mL) in a round-bottomed flask. The appropriate piperazine (1.4 mol equiv.) was then added, together with an additional volume of toluene (3.5 mL). The reaction mixture was then stirred at RT for 1 h, before being stirred under heating at 110 C for an additional 1 h. The solvent was then removed under reduced pressure. EtOAc (10 mL) was then used to dissolve the residue, after which the organic phase was washed sequentially with aqueous NaHCO3 (sat., 50 mL) and brine (50 mL). The organic layer was dried (Na2SO4), filtered and removed under reduced pressure, resulting in a dark yellow oil. This residue was purified by silica gel column chromatography (90 %EtOAc/MeOH) to obtain the desired products 18 or 19, for which the details are given below.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1008-91-9, 1-(Pyridin-4-yl)piperazine, and friends who are interested can also refer to it.

Reference:
Article; Chakravorty, Santanu; Klein, Hanna F.; Hodson, Luke E.; Rabillier, Matthias; Fang, Zhizhou; Richters, Andre; Pelly, Stephen C.; Rauh, Daniel; Van Otterlo, Willem A.L.; South African Journal of Chemistry; vol. 67; (2014); p. 71 – 79;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1597-32-6, 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. 1597-32-6, name is 2-Amino-6-fluoropyridine, molecular formula is C5H5FN2, 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.

N-(6-Fluoropyridin-2-yl)pivalamide. 6-fluoropyridin-2-amine (13.1 g, 117 mmol) was dissolved in anhydrous pyridine (100 mL), and cooled to 0 C. followed by fast dropwise addition of trimethylacetyl chloride (15.9 mL, 129 mmol) over 2 min. 5 min later, the resulting slurry was stirred over night at room temperature. Partial of the solvent was removed on rotary vacuum. The residue was partitioned between saturated ammonium chloride (200 mL) and EtOAc (200 mL). After separation, the organic layer was washed with brine (50 mL), dried over MgSO4, concentrated on rotary vacuum, and purified on flash chromatography eluting with 2575% EtOAc/Hexanes (1400 mL) to afford the expected product as a white solid(21.4 g, 93% yield); 1H NMR (400 MHz, CDCl3) delta ppm 1.29 (s, 9H), 6.63 (dd, J=8.06, 2.01 Hz, 1H), 7.76 (q, J=8.14 Hz, 1H), 7.85 (s, 1H), 8.09 (dd, J=8.06, 1.76 Hz, 1H); Mass spec. 197.15 (MH+), Calc. for C10H13FN2O196.1

According to the analysis of related databases, 1597-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chaturvedula, Prasad V.; Mercer, Stephen E.; Fang, Haiquan; US2006/94707; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 74784-70-6, 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.74784-70-6, name is 5-(Trifluoromethyl)pyridin-2-amine, molecular formula is C6H5F3N2, molecular weight is 162.1125, as common compound, the synthetic route is as follows.

Sodium hydride (60% in paraffin oil, 0.0907 g, 2.27 mmol) was washed twice under Ar with n-hexane (2 ml). A solution of 2-amino-5-chloropyridine (0.250 g, 1.51 mmol) in 2-MeTHF (2.0 ml) was added slowly. The brown-red suspension was stirred until no more gas evolution was observed and then 3-methyl-2-oxazolidinone (0.3 12 g, 3.02 mmol) wasadded. The resulting reaction mixture was stirred at room temperature for 20 h. The reaction was quenched by careful addition of water and diluted with EtOAc. Phases were separated and aqueous phase was extracted with EtOAc (2x). The combined organic layers were washed with brine, dried over anhydrous Na2504 and evaporated under reduced pressure to afford a crude residue (0.457 g). Quantitative 1H NMR analysis using trimethoxy benzeneas an internal standard indicated purity of 45% (52% chemical yield). The crude product was purified by silica gel chromatography (eluting with 1-4% MeOH in DCM) to afford 1-(2- hydroxyethyl)-1 -methyl-3-[5-(trifluoromethyl)-2-pyridyl]urea (0.177 g, 99% purity, 44%) as a pale yellow solid.1H NMR (400MHz, d6DMSO) 69.56 (br, 1H), 8.56 (dd, J = 1.5, 0.7 Hz, 1H), 8.03 (dd, J =9.0, 2.6 Hz, 1H), 7.97-7.93 (m, 1H), 5.42 (br, 1H), 3.62 (q, J = 4.9 Hz, 2H), 3.46-3.38 (m,2H), 2.96 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 74784-70-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SMITS, Helmars; GHORAI, Sujit, Kumar; (25 pag.)WO2017/186624; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 620-08-6, Adding some certain compound to certain chemical reactions, such as: 620-08-6, name is 4-Methoxypyridine,molecular formula is C6H7NO, 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 620-08-6.

4-Trifluoromethyl bromobenzene (4.2ml, 30mmol) was added portionwise to magnesium turnings (0.729g, 30mmol) in dry TEtaF (30ml), a couple of drops of 1,2-dibromoethane was added to initiate the reaction. The resulting brown solution was cooled to -250C. 4-Methoxypyridine (3.0ml, 30mmol) was added followed by benzyl chloroformate (4.3ml, 30mmol). The reaction was stirred for 30 mins at -200C then quenched with 2N HCl. After stirring for 10 mins the mixture was extracted with EtOAc (x3). The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography (silica, 10-40% EtOAc/hexanes) to give the dihydropyridine (9.3Og, 83%). 1H NMR (500 MHz, CDCl3) delta: 2.77 (IH, d, J 16.6), 3.18 (IH, dd, J 7.7, 16.6), 5.20 (IH, d, J 12.0), 5.27 (IH, d, J 12.0), 5.42 (IH, d, J 8.3), 5.77 (IH, d, J 6.3), 7.24-7.37 (7H, m), 7.54 (2H, d, J 8.2), 8.00 (IH, m).

According to the analysis of related databases, 620-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2006/43064; (2006); 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. 69716-28-5, name is N-Hydroxypicolinimidoyl chloride, molecular formula is C6H5ClN2O, 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. Formula: C6H5ClN2O

1-B. Alternative Preparation of ethyl 3-(pyridin-2-yl)-4-(trifluoromethyl)isoxazole-5- carboxylate; [00112] To a solution of (Z)-ethyl 2-bromo-4,4,4-trifluorobut-2-enoate (1.58 g, 6.39 mmol) and (E,Z)-N-hydroxypicolinimidoyl chloride (2.0 g, 12.8 mmol) in ethyl acetate (10 mL) was added indium (III) chloride (0.283 g, 1.28 mmol). The resulting mixture was stirred for 30 minutes under nitrogen, and then potassium hydrogen carbonate (0.959 g, 9.58 mmol) was added. The reaction mixture was stirred for 14 h. The mixture was filtered, and the solid was rinsed with ethyl acetate (10 ml). The filtrate was washed with a saturated aqueous solution of ammonium chloride (10 mL), washed with brine (10 mL), and concentrated. The residue was purified by flash silica gel chromatography using EtOAc/Hexane as the solvent. The fractions containing the product were pooled and concentrated to give the product as an oil (1.15g, 63% yield) as a mixture of the desired isomer, ethyl 3-(pyridin-2-yl)-4- (trifluoromethyl)isoxazole-5-carboxylate and the undesired isomer, ethyl 3-(pyridine- 2-yl)-5-(trifluoromethyl)isoxazole-4-carboxylate in a ratio of approximately 30: 1. MS m/e 287.02 (M+H+); 1H NMR (DMSO, 400 MHz) delta 8.73 (d, J = 4.0 Hz, IH), 8.01(m, IH), 7.87(d, J = 8.0 Hz, IH), 7.65(m, IH), 4.53 (q, J = 8.0 Hz, 2H,), 1.46 (t, J = 8.0 Hz, 3H); HPLC (XBridge 5mu Cl 8 4.6×50 mm, 4 mL/min; Solvent A: 10 % MeOH/water with 0.2 % H3PO4; Solvent B: 90 % MeOH/water with 0.2 % H3PO4, gradient with 0-100 % B over 4 minutes): 3.57 minutes.

With the rapid development of chemical substances, we look forward to future research findings about 69716-28-5.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PITTS, William, J.; DYCKMAN, Alaric, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; WO2010/85582; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 13466-41-6 ,Some common heterocyclic compound, 13466-41-6, molecular formula is C6H7NO, 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.

Step 1 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic Acid Methyl Ester; To a 25 ml round-bottomed flask was added 2-Hydroxy-4-methylpyridine (17.9 mg, 0.164 mmol), 3-Iodo-5-nitro-benzoic acid methyl ester (40 mg, 0.137 mmol), CuI (5.2 mg, 0.027 mmol) and 1,4-dioxane (10 ml). The reaction mixture was stirred for 5 minutes to the dissolve 2-Hydroxy-4-methylpyridine and 3-iodo-5-nitro-benzoic acid methyl ester, after which 1,10-phenanthroline (9.84 mg, 0.055 mmol) was added, followed by K3PO4 (174 mg, 0.082 mmol). The reaction mixture was flushed with N2, and heated to 110 C. for 24 hours. After cooling to room temperature, the mixture was diluted with H2O, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography to give 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester (39.45 mg, 61%) as light yellow solid. MS (M+H)=289.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13466-41-6, its application will become more common.

Reference:
Patent; Roche Palo Alto LLC; US2009/163502; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem