Category: pyridine-derivatives

Reference of 1134327-98-2, 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 1134327-98-2, name is Ethyl 7-bromoimidazo[1,2-a]pyridine-3-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Step 3: 7-Bromoimidazo[1 ,2-a]pyridine-3-carboxylicEthyl 7-bromoimidazo[1 ,2-a]pyridine-3-carboxylate (step 2)(30.81 g, 1 14 mmol) in MeOH (172 ml) was treated with 2M NaOH (172 ml, 343 mmol) and the mixture was heated to 60C for 40 minutes. The volatile solvent was removed in vacuo and the crude material was treated with 2M sodium bisulfate solution to adjust the pH to 6-7. The resulting solid was collected by filtrationand added to water (400 ml). The mixture was stirred and heated to 90C for 1 h. After cooling to RT, the suspension was filtered and dried in a vacuum over at 40C to afford the title product;LC-MS: Rt 0.59 mins; MS m/z 243.1 {M+H}+; Method 2minl_C_v003

According to the analysis of related databases, 1134327-98-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; IRM LLC; BRUCE, Ian; CHAMOIN, Sylvie; COLLINGWOOD, Stephen Paul; FURET, Pascal; FURMINGER, Vikki; LEWIS, Sarah; LOREN, Jon Christopher; MOLTENI, Valentina; SAUNDERS, Alex Michael; SHAW, Duncan; SVIRIDENKO, Lilya; THOMSON, Christopher; YEH, Vince; JANUS, Diana; WEST, Ryan; WO2013/30802; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 126832-81-3, 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 126832-81-3 as follows.

27c) 1-(4-Pyridyl)-4-piperidone Hydrazone Hydrazine monohydrate (1 ml) was added to a solution of 1-(4-pyridyl)-4-piperidone (1.76 g) in methanol (18 ml), and the mixture was stirred at room temperature for 1 hour. The solvent was distilled off, and the residue was crystallized with methanol-ether to obtain the title compound as pale yellow crystals (1.76 g, 92%). NMR (CDCl3) delta: 2.50 (2H, t, J=6.2), 2.61 (2H, t, J=6.2), 3.54 (2H, t, J=6.2), 3.63 (2H, t, J=6.2), 4.99 (2H, bs), 6.60 (2H, d, J=6.6), 8.27 (2H, d, J=6.6).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,126832-81-3, its application will become more common.

Reference:
Patent; Kubo, Keiji; Miyawaki, Toshio; Kawamura, Masaki; US2003/187023; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 139042-59-4, 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.139042-59-4, name is 5-Acetyl-2-bromopyridine, molecular formula is C7H6BrNO, molecular weight is 200.03, as common compound, the synthetic route is as follows.

A mixture of compound J-1 (25 g, 125.6 mmol), NBS (24.5 g, 138.2 mmol) and p-TSA (3.4 g, 20.9 mmol) wasstirred at 100 C under N2 for 2 hours. The mixture was then cooled to rt and dissolved in DCM. The resulting mixturewas quenched with water and extracted with DCM (50 mL x 3). The combined organic phases were dried over anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc (v/v) =5/1) to give the title compound J-2 (25 g, 71%). The compound was characterized by the following spectroscopic data:MS-ESI: m/z 279.9 [M+H]+; and1H NMR (400 MHz, CDCl3): delta 8.95 (d, J = 1.12 Hz, 1H), 8.11-8.14 (m, 1H), 7.66-7.68 (m, 1H), 4.41 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 139042-59-4, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; LUO, Huichao; YU, Tianzhu; TAN, Yumei; EP2730572; (2015); B1;,
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Pyridine | C5H5N – PubChem

Reference of 932-35-4, 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 932-35-4, name is 3-Hydroxypicolinonitrile. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-hydroxypyridine-2-carbonitrile d (10 mmol, 1.2 g), chloroacetone (1 equiv. , 10 mmol, 0.93 g) and potassium carbonate (1 equiv., 10 mmol, 1.38 g) in DMF (30 ml) was heated at 80C overnight. The reaction mixture was poured into ice-water (200 ml) and the precipitate was filtered off and dried to afford intermediate e (1.4 g, yield = 80%, purity (LC) > 95%). To a stirred mixture of intermediate e (7.9 mmol, 1.39 g) and cyanoacetic acid (1 equiv. , 7.9 mmol, 0.675 g) in DMF (20 ml) was added EDCI (1 equiv. , 7.9 mmol, 1.51 g) and the reaction mixture was stirred overnight at room temperature. The mixture was poured into ice-water (150 ml) causing a precipitation. The solid was filtered off and dried by co-evaporation with tetrahydrofuran and then with toluene. The residue was mixed with isopropanol (15 ml) and ethyl-diisopropylamine (1 equiv., 7.9 mmol, 1.02 g) and heated to 80C during 4h. After cooling to room temperature, a solid was filtered off affording intermediate f (1.35 g, yield = 76%, purity (LC) > 95%). A mixture of intermediate f (1.0 mmol, 0.225 g), copper (II) acetate(2 equiv. , 2.0 mmol, 0.363 g), 4-nitrophenylboronic acid (2.0 equiv. , 2.0 mmol, 0.334 g), triethyl- amine (2.0 equiv. , 2.0 mmol, 0.202 g) and pyridine (2.0 equiv. , 2.0 mmol, 0.158 g) in dichloromethane (5 ml) was stirred overnight at room temperature in a reaction vial provided with a calcium chloride tube. The reaction mixture was dilluted with dichloromethane (50 ml), washed with water, dried (MgS04), filtered and evaporated under reduced pressure. The crude compound was purified by chromatography (silica gel, eluent: 2% methanol in dichloromethane) to afford compound 3 (30 mg, yield = 8 %, purity (LC) = 82 %).

According to the analysis of related databases, 932-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TIBOTEC PHARMACEUTICALS Ltd.; WO2005/111044; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 74420-15-8 ,Some common heterocyclic compound, 74420-15-8, molecular formula is C7H5BrN2, 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.

[0193] In a microwave tube was placed ethyl 2-bromothiazole-4-carboxylate (944 mg, 4 mmol), 3-bromo-1H-pyrrolo[2,3-blpyridine (867 mg, 4.40 mmol), and K2C03 (663 mg, 4.80 mmol). The tube was sealed and DMSO (7.5 ml) was added. The mixture was heated at 150C for 3 h. The mixture was poured into EtOAc/H20 (30 mL/30 mL). The organic was dried (Na2504) and filtered. After removal of the solvent, the product was purified (twice) by silica gel chromatography using 10-20% EtOAc/hexane as the eluent to give ethyl 2-(3- bromo- 1 H-pyrrolo[2,3 -blpyridin- 1 -yl)thiazole-4-carboxylate (587 mg, 1.667 mmol, 41.7% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,74420-15-8, its application will become more common.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1060811-62-2, 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.1060811-62-2, name is 4,6-Dichloronicotinaldehyde, molecular formula is C6H3Cl2NO, molecular weight is 176, as common compound, the synthetic route is as follows.

To a reaction vessel containing a mixture of 4,6-dichloronicotinaldehyde (300 g, 1.7 mol) in 1,4- dioxane (1200 mL) was added hydrazine (50%> in water)(360 mL, 3.6 mol). The reaction vessel was sealed and heated at 150 C over 18 h. The mixture was cooled to room temperature, concentrated in vacuo, poured over water and filtered. The filter cake was washed with 20%> EtOAc in hexanes and dried to afford 6-chloro-lH-pyrazolo[4,3-c]pyridine (101.4 g, 38 %>) as a light-yellow solid. LCMS (ESI) [M+H]+ = 154.

The chemical industry reduces the impact on the environment during synthesis 1060811-62-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GENENTECH, INC.; BRYAN, Marian C.; CHAN, Bryan; DIEDERICH, Francois; DOTSON, Jennafer; HANAN, Emily; HEFFRON, Timothy; LAINCHBURY, Michael; HEALD, Robert; SEWARD, Eileen M.; WO2014/210354; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84249-14-9, 2-Amino-4-bromopyridine, 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, Quality Control of 2-Amino-4-bromopyridine, blongs to pyridine-derivatives compound. Quality Control of 2-Amino-4-bromopyridine

Step 1: N-(4-bromopyridin-2-yl)acetamide To a solution of 4-bromopyridin-2-amine (12.0 g, 69.4 mmol) in acetic anhydride (240 mL) was added DMAP (0.0847 g, 0.694 mmol). The reaction mixture was allowed to stir at 140 C. for 3 h and then allowed to cool to rt. Ice water was added and the pH of the mixture was adjusted to 8.5 by the addition of concentrated NH4OH. The solid which precipitated was filtered, washed with cold water and hexanes, and dried to give N-(4-bromopyridin-2-yl)acetamide (13.3 g, 89%) as a white solid.

The synthetic route of 84249-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; Bharathan, Indu T.; Blackburn, Chris; Ciavarri, Jeffrey P.; Chouitar, Jouhara; Cullis, Courtney A.; D’Amore, Natalie; Fleming, Paul E.; Gigstad, Kenneth M.; Gipson, Krista E.; Girard, Mario; Hu, Yongbo; Lee, Janice; Li, Gang; Rezaei, Mansoureh; Sintchak, Michael D.; Soucy, Francois; Stroud, Stephen G.; Vos, Tricia J.; Wong, Tzu-Tshin; Xu, He; Xu, Tianlin; Ye, Yingchun; US2015/225422; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 630120-99-9, 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.630120-99-9, name is 5-(Benzyloxy)-2-bromopyridine, molecular formula is C12H10BrNO, molecular weight is 264.1179, as common compound, the synthetic route is as follows.

To a solution of 5-(benzyloxy)-2-bromopyridine (200 mg, 0.757 mmol), methanamine (70.6 mg, 2.272 mmol) and sodium 2-methylpropan-2-olate (437 mg, 4.54 mmol) in THF (5 mL) was added Pd2dba3 (69.3 mg, 0.076 mmol) and dicyclohexyl(2?,4?,6?-triisopropyl-[1,1?-biphenyl]-2-yl)phosphine (36.1 mg, 0.076 mmol). The reaction mixture was stirred at 60 C. for 15 h. The mixture was cooled and diluted with water (10 mL). After the mixture was extracted with EtOAc (10 mL×3), the combined organic fractions were washed with water (20 mL×3), dried (anhydrous Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by prep-TLC (1/1 petroleum ether/EtOAc) to give the title compound. MS: 215 (M+1).

Statistics shows that 630120-99-9 is playing an increasingly important role. we look forward to future research findings about 5-(Benzyloxy)-2-bromopyridine.

Reference:
Patent; BAO, JIANMING; GAO, XIAOLEI; KNOWLES, SANDRA L.; LI, I, CHUNSING; LO, MICHAEL MAN-CHU; MAZZOLA, Jr., ROBERT D.; ONDEYKA, DEBRA L.; STAMFORD, ANDREW W.; ZHANG, FENGQI; (214 pag.)US2017/183342; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1214334-70-9, 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.1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid, molecular formula is C7H6BrNO3, molecular weight is 232.0314, as common compound, the synthetic route is as follows.

To a solution of 5-bromo-6-methoxy picolinicacid1 (1.5 g, 0.00646 mol) in DMF (15mL, 10 vol), cooledto 0oC Na2CO3 (685 mg, 0.00646 mol) and MeI (0.834 mL,0.0129 mol) were added and the mixture was stirred for 16hat room temperature. Water was added, extracted with ethylacetate, concentrated under reduced pressure to obtain 5-bromo-6-methoxy-pyridine-2-carboxylic acid methyl ester(1.5 g, 0.00609 mol) in EtOH (15mL), NH2NH2.H2O (1.21 g,0.0243 mol) was added and the mixture was stirred for 3h at70oC, cooled to room temperature, solvents were evaporated,water (15mL) was added, filtered the reaction mass, to givepure compound 2.

Statistics shows that 1214334-70-9 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-6-methoxypicolinic acid.

Reference:
Article; Namani, Vasu; Goud, B. Bharath Kumar; Kumari, Y. Bharathi; Kumbham, Ramesh; Letters in Organic Chemistry; vol. 13; 4; (2016); p. 249 – 254;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 5470-70-2, name is Methyl 6-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows. category: pyridine-derivatives

Step 1: Intermediate 31-b [0181] To a solution of methyl 6-methylnicotinate 31-a (20.10 g, 133 mmol) in THF (90 ml) cooled to 0° C. was added drop wise a 1.0 M solution of LiAlH4 in THF (100 ml, 100 mmol) and the reaction was then stirred at 0° C. for 1 hour. Water (3.8 ml) was slowly added, followed by 15percent NaOH (3.5 ml) and water (11.4 ml) and the mixture was stirred at room temperature for 1 hour. The reaction was filtered over celite and volatiles were removed in vacuo to provide intermediate 31-b as a yellow oil.

With the rapid development of chemical substances, we look forward to future research findings about 5470-70-2.

Reference:
Patent; Pharmascience, Inc.; Laurent, Alain; Rose, Yannick; Jaquith, James B.; US2015/191473; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem