Pyridine-derivatives

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. 98400-69-2, name is 4-(Boc-Amino)pyridine. A new synthetic method of this compound is introduced below., Product Details of 98400-69-2

Preparation of 4-Aminopyridin-3-ylboronic acid hydrochloride saltPart AUnder a nitrogen atmosphere, a solution of n-butyllithium in hexane (100 mL of 2.5 M, 250 mmol) was added over 20 minutes to a stirred solution of tert-butyl pyridin-4-ylcarbamate (19.4 g, 100 mmol) and N,N,N’,N’-tetramethylethylenediamine (TMEDA) (31.4 g, 270 mmol) in tetrahydrofuran (THF) (500 mL) at -78° C. tert-Butyl pyridin-4-ylcarbamate is available from a literature procedure (Spivey, A. C. et al. J. Org. Chem. 1999, 64, 9430-9443). A white solid appeared and the mixture was stirred for 10 minutes at -78° C., was transferred to a salt bath, and allowed to warm slowly to -4° C. over about two hours before cooling to -78° C. again. Trimethyl borate (39.5 g, 380 mmol) was added over 15 minutes. The solution was warmed to 0° C. and poured into saturated aqueous ammonium chloride (500 mL). The mixture was stirred for 2 minutes. After standing at room temperature overnight, the mixture was partitioned between diethyl ether and brine. The organic layer was separated and washed with brine and then diluted to a volume of 3 liters with the addition of diethyl ether. A white solid formed in the organic layer and was isolated by filtration. The solid was washed sequentially with diethyl ether, water, and diethyl ether, then was dried to provide 17.1 g of 4-[(tert-butoxycarbonyl)amino]pyridin-3-ylboronic acid as a white solid.

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, 98400-69-2, 4-(Boc-Amino)pyridine.

Reference:
Patent; Coley Pharmaceutical Group, Inc.; US2011/269965; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 67367-26-4 , The common heterocyclic compound, 67367-26-4, name is Methyl 2-methoxynicotinate, molecular formula is C8H9NO3, 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 2-methoxynicotinate was synthesized from ethyl 2-chloronicotinate with sodium methoxide as in Example 4. A 50 mL flask was charged with methyl 2-methoxynicotinate (2.50 g, 0.015 mol), 10 mL dry DMF and 60% NaH (0.745 g, 0.0186 mol) with magnetic stirring. 3?-Fluoro-4?-methoxyacetophenone (2.60 g, 0.0155 mol) in 6 mL anhydrous DMF was added over 5-10 min. After addition, the reaction mixture was stirred for 30 min. The mixture was poured into 50 mL NH4Cl solution, the yellow solid was filtered and further washed with water and purified by column chromatography (hexane:EtOAc 4:1) to get (3.0 g, 66.4%) of product. A 50 mL flask was charged with this product (0.8 g, 2.64 mmol) and pyridine hydrogen chloride (3.04 g, 26.4 mmol) and heated to 190 C. for 4 h. The mixture was poured into sodium bicarbonate solution and the solid was collected by filtration, washed with EtOAc and MeOH and passed through a column (methanol:dichloromethane 1:4) to afford 400 mg of 2-(3-fluoro-4-hydroxyphenyl)pyrano[2,3-b]pyridine-4-one (59%). MS (ES) m/z: 257.85 (M); Mp. 267-268 C.

The synthetic route of 67367-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RVX Therapeutics Inc.; McLure, Kevin G.; Young, Peter R.; US2013/281396; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 66572-56-3, 2-Bromoisonicotinic 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, Recommanded Product: 2-Bromoisonicotinic acid, blongs to pyridine-derivatives compound. Recommanded Product: 2-Bromoisonicotinic acid

Example 1-88 4-(2-Bromo-4-pyridinyl)-7V-(3-methylphenyl)-l,3-thiazol-2-amine (154). [0360] 2-Bromo-7V-methyl-7V-(methyloxy)-4-pyridinecarboxamide (151). Et3N(14.9 mL, 107 mmol) was added to a stirred suspension of 2-bromo-4- pyridinecarboxylic acid (5.40 g, 26.7 mmol), EDCI (5.64 g, 29.4 mmol), HOBT (3.97 g, 29.4 mmol) and MeNHOMe-HCl (3.91 g, 40.0 mmol) in dry DCM (100 mL), and the mixture was stirred at 20 0C for 16 h. The resulting solution was diluted with DCM (200 mL) and washed with water (2 x 50 mL), washed with brine (50 mL), dried and the solvent evaporated. The residue was purified by column chromatography, eluting with 50% EtO Ac/pet, ether, to give amide 151 (4.56 g, 70%) as an oil: 1H NMR (CDCl3) delta 8.45 (d, J= 5.0 Hz, 1 H, H-6), 7.72 (br s, 1 H, H-3), 7.48 (dd, J= 5.0, 1.3 Hz, 1 H, H-5), 3.56 (s, 3 H, OCH3), 3.67 (s, 3 H, NCH3); MS m/z 245.3/247.3 (MH+, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,66572-56-3, 2-Bromoisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY; AUCKLAND UNISERVICES LIMITED; WO2009/114552; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58584-63-7, (6-Methoxypyridin-3-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, Recommanded Product: 58584-63-7, blongs to pyridine-derivatives compound. Recommanded Product: 58584-63-7

Step 2: 5-Chloromethyl-2-methoxy-pyridine Thionyl chloride (9.2 mL, 126 mmol) was added dropwise to a solution of (6-methoxy-pyridin-3-yl)-methanol (1.00 g, 7.2 mmol) in dichloromethane (38 mL). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated and dichloromethane (100 mL) was added. The solution was washed with saturated aqueous sodium hydrogen carbonate (this resulted in bubbling). The organic layer was separated and the aqueous layer was extracted with dichloromethane (2*100 mL). The combined organic layers were washed with brine (150 mL), dried (sodium sulfate), filtered, and evaporated to give 5-chloromethyl-2-methoxy-pyridine (995 mg, 88%) as a clear oil.

The synthetic route of 58584-63-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Banner, Bruce Lester; Bilotta, Joseph Anthony; Fotouhi, Nader; Gillespie, Paul; Goodnow, Robert Alan; Hamilton, Matthew Michael; Haynes, Nancy-Ellen; Kowalczyk, Agnieszka; Mayweg, Alexander; Myers, Michael Paul; Pietranico-Cole, Sherrie Lynn; Scott, Nathan Robert; Thakkar, Kshitij Chhabilbhai; Tilley, Jefferson Wright; US2007/49632; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113682-56-7, 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. 113682-56-7, name is 1,4-Di(pyridin-4-yl)benzene. A new synthetic method of this compound is introduced below.

Comparative compound 2 is synthesized by the following method. 0.5 g (2.2 mmol) of 1,4-di(4-pyridyl)benzene, 1.3 g (6.6 mmol) of cyanobenzyl bromide, and 20 ml of DMF were placed in a 100 ml eggplant-shaped flask, Followed by stirring at 100 C. for 8 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, the concentrated system was dispersed in ethyl acetate and washed, and the precipitated crystals were filtered and washed with ethyl acetate to obtain 1.0 g (yield 73% ) Was obtained.Subsequently, 0.5 g (0.8 mmol) of the Br compound of Comparative Compound 2 was changed to an aqueous solution, and an aqueous solution of 0.4 g (2.5 mol) of ammonium hexafluorophosphate was added dropwise, followed by stirring for 2 hours. After completion of the reaction, the precipitated white crystals were filtered, washed with water and dried at 50 C. under reduced pressure to obtain 0.48 g (yield 80%) of Comparative Compound 2

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113682-56-7, its application will become more common.

Reference:
Patent; CANON INCORPORATED; TAMURA, TETSUYA; IGAWA, SATOSHI; YAMADA, KENJI; (27 pag.)JP2017/197477; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17228-75-0, 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. 17228-75-0, name is 2,6-Dichloro-4-methoxypyridine. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloro-4-methoxypyridine (18.1 g, 102 mmol) in sulfuric acid (110 mL) was added nitric acid (15.6 mL) dropwise at 0 C., and then the mixture was heated to 100 C. for 2 hours. The reaction mixture was poured into ice-water, the suspension was filtered and washed with water to obtain 2,6-dichloro-4-methoxy-3-nitropyridine as a white solid (19.9 g, 88% yield). MS (ESI) calcd for C6H4Cl2N2O3: 221.96.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17228-75-0, 2,6-Dichloro-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1246349-97-2, 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.1246349-97-2, name is 4-Chloro-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-c]pyridine, molecular formula is C14H11ClIN3O, molecular weight is 399.61, as common compound, the synthetic route is as follows.

Intermediate 14 Cyclohexyl-[3-iodo-1-(4-methoxy-benzyl)-1H-pyrazolo[4,3-c]pyridin-4-yl]-amine To a solution of Intermediate 13 (0.95 g, 2.4 mmol) in 1-butanol (5 ml) at room temperature was added cyclohexylamine (1.1 ml, 9.52 mmol). The resulting mixture was irradiated at 190 0C for 1 h in a Biotage I-60 microwave reactor. The reaction mixture was then evaporated to dryness and the crude residue was purified by flash chromatography eluting with 10 to 100% ethyl acetate/petroleum ether gradient to give a white solid (0.87 g, 80%) 1H NMR (400 MHz1 DMSO-d6) delta ppm 1.24 – 1.50 (m, 5 H), 1.50 – 1.63 (m, 1 H), 1.63 – 1.80 (m, 2 H), 1.86 – 2.03 (m, 2 H), 3.72 (s, 3 H), 4.02 – 4.15 (m, 1 H), 5.43 (s, 2 H), 5.95 (d, .7=7.3 Hz, 1 H), 6.85 – 6.90 (m, 2 H), 6.95 (d, J=6.0 Hz, 1 H), 7.15 – 7.24 (m, 2 H), 7.76 (d, J=6.0 Hz, 1 H); m/z (ES+APCI)+: 463 [M + H]+.

Statistics shows that 1246349-97-2 is playing an increasingly important role. we look forward to future research findings about 4-Chloro-3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-c]pyridine.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; MCIVER, Edward, Giles; SMILJANIC, Ela; HARDING, Denise, Jamilla; HOUGH, Joanne; WO2010/106333; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 86873-60-1, 5-Chloro-2-picolinic 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, Application In Synthesis of 5-Chloro-2-picolinic acid, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Chloro-2-picolinic acid

To a stirred solution of tert-butyl (l-aminopiperidin-4-yl)carbamate (500 mg, 2.32 mmol, 1.0 equiv) in DMF (05 mL) was added HATU (1763 mg, 4.64 mmol, 2.0 equiv) at RT and stirred for 10 minutes Then 5-chloropicolinic acid (365 rng, 2.32 mmol, 1.0 equiv) was added followed by the addition of DIPEA (1.2 mL, 6.96 mmol, 3.0 equiv). The resulting reaction mixture was allowed to stir at RT for overnight. Product formation was confirmed by LCMS. the reaction mixture was diluted with water (50 mL) and extracted with EtOAc (50 mL c 2). The combined organic layer was washed with water (30mL), brine solution (30 mL x 2), dried over anhydrous sodium sulfate and concentrated under reduced pressure, to obtain tert-butyl (l-(5- chloropicolinamido)piperidin-4-yl)carbamate (500 mg, 60 % Yield) as an off white solid. LCMS 355.1 [M+H]+; i XMR (400 MHz. DMSO-cA) d 9.61 (s, 1 H), 8.66 (d, J=2.19 Hz, 1 H), 8.11 (dd, J==8.33, 2.19 Hz, 1 H), 7.99 id. =8.33 Hz, 1 H), 6.83 (d, ./ 7.02 Hz, 1 H), 3.23 (br. s., 1 H), 2.84 – 3.00 (m, 3 H), 2.62 – 2.84 (m, 2 H), 1 73 (d, J=l 1.40 Hz, 2 H), 1.47 – 1.66 (m, 2 H), 1 38 (s. 9 1 1}

The synthetic route of 86873-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PRAXIS BIOTECH LLC; DELGADO OYARZO, Luz Marina; URETA DIAZ, Gonzalo Andres; PUJALA, Brahmam; PANPATIL, Dayanand; BERNALES, Sebastian; CHAKRAVARTY, Sarvajit; (0 pag.)WO2019/236710; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16179-97-8, 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. 16179-97-8, name is 2-(Pyridin-2-yl)acetic acid hydrochloride, molecular formula is C7H8ClNO2, 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.

Example : 8; 8- (2-isobutoxybenzyl)-2- (pyridin-2-ylacetyl)-2, 8-diazaspiro [4.5] decane; Scheme 1; a) tert-butyl 2- (pyridin-2-ylacetyl)-2, 8-diazaspiro [4.5] decane-8-carboxylate; To a solution of tert-butyl 2,8-diazaspiro [4.5] decane-8-carboxylate hydrochloride (800mg, 2. 89mmol, 1 equiv), 2-pyridylacetic acid hydrochloride (500mg, 2. 89mmol, 1 equiv) and triethylamine (1. 2ml, 8. 68mmol, 3 equiv) in dry dichloromethane (12ml), was added 0-(7-azabenzotriazol-1-yl)-N, N, N, N’-tetramethyluronium hexafluorophosphate (1. 1 g, 2.89mmol, 1 equiv). The reaction mixture was stirred at room temperature for 3 hours, then concentrated, and partitioned between ethyl acetate and saturated sodium hydrogen carbonate. The organic layer was isolated, dried (MgS04) and concentrated to give a dark orange oil which was subjected to silica-gel chromatography using a mixture of methanol and dichloromethane (4: 96, v/v) as eluent, to provide the title compound (1.2g, quantitative) as a dark yellow oil. LCMS (Method E): RT = 2.19 minutes; 360 (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 16179-97-8, 2-(Pyridin-2-yl)acetic acid hydrochloride.

Reference:
Patent; ASTRAZENECA AB; WO2005/40167; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 83004-10-8, 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.83004-10-8, name is 2-Bromo-6-(bromomethyl)pyridine, molecular formula is C6H5Br2N, molecular weight is 250.92, as common compound, the synthetic route is as follows.

To a solution of 0.855 ml of diisopropylamine in 15 ml of tetrahydrofuran was added 2.26 ml of a hexane solution containing 2.66 M n-butyllithium at O0C, followed by stirring the reaction mixture at 00C for 30 minutes. After cooling down to -78C, a solution of 1.54 g of 1- tert-butyl 4-ethyl piperidine-l,4-dicarboxylate in 5 ml of tetrahydrofuran was added to the reaction mixture, and the resultant mixture was stirred at -78C for 30 minutes. A solution of 1.00 g of 2-bromo-6-(bromomethyl)pyridine in 5 ml of tetrahydrofuran was added to the reaction mixture, followed by stirring the reaction mixture at -78C for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extracting with ethyl acetate. The resulting ethyl acetate solution was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate = 20/1 – 2/1) to give the title compound as a yellow oil.

The chemical industry reduces the impact on the environment during synthesis 83004-10-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; WO2009/104802; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem