Pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 127356-38-1, 2-Methoxy-5-nitropyridin-4-amine, 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, Recommanded Product: 2-Methoxy-5-nitropyridin-4-amine, blongs to pyridine-derivatives compound. Recommanded Product: 2-Methoxy-5-nitropyridin-4-amine

A solution of 15.51 g of 2-methoxy-5-nitropyridin-4-amine (example E7) in 1.55 l methanol is treated with 4.65 g Pd/C (10% Pd) and hydrogenated for 12 h under atmospheric pressure. The reaction mixture is filtered through a plug of celite and the filtrate is concentrated under vacuum. The resulting residue is treated with 181 ml formic acid and the mixture is refluxed for 50 h. The formic acid is distilled off and the residue is repeatedly purified by flash chromatography (neutral alumina oxide, ethyl acetate / methanol) to yield the title compound. 1H NMR (200 MHz, D6-DMSO): delta = 3.87 (s, 3H), 6.85 (d, J = 0.9 Hz, 1H), 8.24 (s, 1 H), 8.54 (d, J = 0.9Hz, 1 H), 12.5 (bs, 1 H). MS (MH+ found) = 150.1

At the same time, in my other blogs, there are other synthetic methods of this type of compound,127356-38-1, 2-Methoxy-5-nitropyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; 4SC AG; EP2017277; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 83766-88-5, 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.83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, molecular weight is 151.21, as common compound, the synthetic route is as follows.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

Statistics shows that 83766-88-5 is playing an increasingly important role. we look forward to future research findings about 2-(tert-Butoxy)pyridine.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 192447-58-8, 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.192447-58-8, name is 2,6-Dibromo-N,N-dimethylpyridin-4-amine, molecular formula is C7H8Br2N2, molecular weight is 279.9598, as common compound, the synthetic route is as follows.

Stage 1: Synthesis of 2,6-dibromo-4-(dimethylamino)pyridine-3,5-dicarbaldehyde 1 mole of 2,6-dibromo-4-(dimethylamino)pyridine may be treated with 2 moles of hexamethylenetetramine in trifluoroacetic acid at reflux for three hours. The solvent may be removed with a thin-film evaporator at elevated temperature and under reduced pressure. The residue may be dissolved in 1M hydrochloric acid, extracted with dichloromethane, and the organic phase may be isolated. The organic phase may be washed with brine and the solvent may be removed with a thin-film evaporator at elevated temperature and under reduced pressure to afford 2,6-dibromo-4-(dimethylamino)pyridine-3,5-dicarbaldehyde.

The chemical industry reduces the impact on the environment during synthesis 192447-58-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Martineau, Louis C.; US2014/135359; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1133879-69-2, 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.1133879-69-2, name is 3-Fluoro-5-vinylpyridine, molecular formula is C7H6FN, molecular weight is 123.1277, as common compound, the synthetic route is as follows.

General procedure: A mixture of tetrahydrocarbazole 5a (0.17 g,1 mmol), 5fluoro3vinylpyridine (6) (0.12 g, 1 mmol), CsF(0.1 g), and hydroquinone (0.02 g) in DMSO (1.5 mL) was heated with stirring at 130-140 C for 4 h, DMSO was evaporatedin vacuo (3 Torr), the product was extracted from residue withdichloromethane. The solvent was evaporated and the residuewas subjected to chromatography on silica gel (60 mesh), eluentmethanol-chloroform = 1 : 5. The yield was 0.22 g (75%), m.p.65-67 C. Found (%): C, 77.63; H, 6.43; N, 9.64. C19H19FN2.Calculated (%): C, 77.52; H, 6.45; N, 9.52. 1H NMR (DMSOd6), : 1.81 (m, 4 H, CH2); 2.29 (m, 2 H, CH2); 2.72 (m, 2 H,CH2); 3.05 (t, 2 H, CH2Py, J = 6.8 Hz); 4.25 (t, 2 H, CH2N,J = 6.9 Hz); 6.80 (dt, 1 H, CHPy, JHF = 9.3 Hz, JHH = 2.4 Hz);7.05-7.30 (m, 3 H, CHAr); 7.50 (d, 1 H, CHAr, J = 6.8 Hz); 8.14(s, 1 H, CHPy); 8.34 (d, 1 H, CHPy, JHH = 2.4 Hz). 19F NMR(DMSOd6), : -49.38 (d, JFH = 9.4 Hz).

Statistics shows that 1133879-69-2 is playing an increasingly important role. we look forward to future research findings about 3-Fluoro-5-vinylpyridine.

Reference:
Article; Sokolov; Aksinenko; Nikolaeva; Grigor’Ev; Kinzirsky; Bachurin; Russian Chemical Bulletin; vol. 63; 5; (2014); p. 1137 – 1141; Izv. Akad. Nauk, Ser. Khim.; 5; (2014); p. 1137 – 1141,5;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 54221-93-1, 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 54221-93-1, name is 2,6-Dimethylisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

4-???2,6-????????????(3)2g?2,6-??????????(2)(??)?100ml?????????1ml?98%??24????????????????NaHCO3???????????60ml?CHCl3?5??????????????????????Na2SO4?????????????????????????50ml??????4????????????????????????????????????????????[?:???????/CH2Cl2(50/50)?CH2Cl2]????1g?4-???2,6-????????????(3)????

According to the analysis of related databases, 54221-93-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CIS BIO INTERNATIONAL, CIS; JP2004/509075; (2004); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60010-03-9, 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloro-4-methyl-3-nitropyridine (6.5g; 31 .4 mmol) and TEA (10g; 3eq) in acetonitrile (200ml) was added (R)-(-)-3-fluoropyrrolidine hydrochloride (4.75g; 1 .2eq). The mixture was stirred for 4h at rt, after which the reaction mixture was quenched with sat NaHCOs(aq) (300ml), diluted with water and and EtOAc. The layers were separeted and the waterlayer was extracted with EtOAc (3x150ml_) untill no UV(254nm) active material was extracted). The combined organic layers were washed with brine and dried over Na2SO4(s). Filtration and in vacuo concentration resulted in a quantitative yield 8.36g of the title compound as a yellow/orange oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; STRØBAeK, Dorte; WO2011/26890; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 898746-42-4 ,Some common heterocyclic compound, 898746-42-4, molecular formula is C7H5FN2, 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.

To a solution of 6-fluoro-1H-pyrrolo[2,3-b]pyridine (2.50 g, 18.36 mmol) in DMF (50 mL) was added a solution of bromine (3.20 g, 20.00 mmol) in DMF (20 mL) at 0 C . After the addition, the mixture was stirred at rt for 2 h. To the mixture was added water (100 mL), then there was a lot of solid precipitated out. The mixture was filtered under reduced pressure, and the filter cake was washed with water (30 mL) for two times and then dried in vacuo at 60 C for 24 h to give the title compound as a white solid (3.44 g, 87%).MS (ESI, pos. ion) m/z: 217.1 [M+H]+1H NMR (400 MHz, DMSO-d6) (ppm): 12.20 (s, 1H), 8.04 – 7.95 (m, 1H), 7.67 (d, J = 2.5 Hz, 1H), 6.94 (t, J = 9.7 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,898746-42-4, its application will become more common.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; REN, Qingyun; TANG, Changhua; LIN, Xiaohong; YIN, Junjun; YI, Kai; (270 pag.)WO2017/97234; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 716362-10-6, 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 716362-10-6, name is 6-Chloro-4-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of 6-chloro-N,4-dimethoxy-N-methylnicotinamide (3) (0673) To a solution of 6-chloro-4-methoxynicotinic acid (1, 25.0 g, 133.6 mmol) in dichloromethane (300 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38.44 g, 200.5 mmol), 1-hydroxybenzotriazole (30.40 g, 200.4 mmol) and N,N-diisopropylethylamine (69.8 mL, 400.8 mmol) were added at 0 C. and stirred the mixture for 5 min. N, O-dimethylhydroxylamine hydrochloride (2, 19.56 g, 200.53 mmol) was then added at same temperature and the reaction was stirred for 16 h at room temperature. After completion, reaction mass was diluted with dichloromethane and washed with cold water. The organic layer was separated and dried over sodium sulphate, filtered and concentrated to give crude. The crude was re-crystallised in ethanol to afford 6-chloro-N,4-dimethoxy-N-methylnicotinamide (3) as white solid. Yield: 19.3 g, 62%; MS (ESI) m/z 231.17 [M+1]+.

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 716362-10-6, 6-Chloro-4-methoxynicotinic acid.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; ERNST, Justin T.; REICH, Siegfried H.; SPRENGELER, Paul A.; TRAN, Chinh Viet; PACKARD, Garrick Kenneth; XIANG, Alan X.; NILEWSKI, Christian; MICHELS, Theo; (478 pag.)US2017/145026; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 175204-80-5, 3-Amino-4-(trifluoromethyl)pyridine, 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 3-Amino-4-(trifluoromethyl)pyridine, blongs to pyridine-derivatives compound. Safety of 3-Amino-4-(trifluoromethyl)pyridine

Example 22. Synthesis of Compound 131 Tert-butyl 4-[[4-(trifluoromethyl)pyridin-3-yl]amino]-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine-7-carboxylate To a stirred mixture of tert-butyl 4-chloro-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine-7-carboxylate (500 mg, 1.854 mmol, 1 equiv.) and 4-(trifluoromethyl)pyridin-3-amine (601.03 mg, 3.707 mmol, 2.0 equiv.) in 1,4-dioxane (5 mL) were added Pd(AcO)2 (83.24 mg, 0.371 mmol, 0.2 equiv.) and Cs2CO3 (1207.95 mg, 3.707 mmol, 2.0 equiv.) and XantPhos (429.04 mg, 0.741 mmol, 0.4 equiv.) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 2 h at 110 degrees C. under nitrogen atmosphere. The reaction was monitored by LCMS. The mixture was allowed to cool down to room temperature. The resulting mixture was filtered, the filter cake was washed with DCM (3*2 mL). The filtrate was concentrated under reduced pressure. The resulting mixture was concentrated under reduced pressure. The crude product was purified by reverse phase flash with the following conditions (Column:C18,120 g; Mobile Phase A:Water/0.05% NH4HCO3, Mobile Phase B:ACN; Flow rate:45 mL/min; Gradient: 45% B to 65% B in 15 min; Detector, 254 nm and 220 nm, the desired product were collected at 64% B) to afford tert-butyl 4-[[4-(trifluoromethyl)pyridin-3-yl]amino]-5H,6H,7H,8H-pyrido[3,4-d]pyrimidine-7-carboxylate (600 mg, 81.86%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,175204-80-5, 3-Amino-4-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; Goldfinch Bio, Inc.; Ledeboer, Mark W.; Daniels, Matthew H.; Yu, Maolin; Harmange, Jean-Christophe P.; US2020/102301; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 51173-05-8, 5-Fluoro-2-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, 51173-05-8, blongs to pyridine-derivatives compound. Safety of 5-Fluoro-2-hydroxypyridine

Intermediate 3 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM? showed intermediate 4 and something else (discarded)). The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford intermediate 4 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of intermediate 4; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product intermediate 4. Total: 117.0+3.6+6.23=126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,51173-05-8, its application will become more common.

Reference:
Patent; Kadow, John F.; Regueiro-Ren, Alicia; US2006/142298; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem