Day: April 12, 2022

Reference of 76006-11-6, 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.76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine, molecular formula is C6H4ClN3, molecular weight is 153.57, as common compound, the synthetic route is as follows.

Pyrazolopyridine 6 (0.44 g, 2.9 mmol) was dissolvedin dry methanol (50 mL) and N-iodosuccinimide (1.0 g,4.4 mmol) was added in portions. The mixture was stirred atroom temperature for 2h. Then, the solvent was removedunder reduced pressure and the residue was extracted withethyl acetate. The combined organic extracts were washedwith aqueous sodium thiosulfate (10% w/v) solution, thendried over sodium sulfate, filtered and concentrated. Thecrude product was purified by column chromatography (silicagel) using a mixture of cyclohexane/ethyl acetate (6/4,v/v) as the eluent to provide pure 7 as a yellow solid, in 99% yield. mp 252-3 C (EtOAc). 1H NMR (600 MHz, DMSO-d6) 7.50 (d, 1H, H-4, J = 5.5Hz), 8.08 (d, 1H, H-5, J =5.5Hz). HR-MS (ESI) m/z: calcd for C6H4ClIN3, [M1+H]+ =279.9133, found 279.9128. Anal. Calcd for C6H3ClIN3: C,25.79; H, 1.08; N, 15.04. Found: C, 25.91; H, 1.13; N, 14.88.

Statistics shows that 76006-11-6 is playing an increasingly important role. we look forward to future research findings about 7-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Article; Gavriil, Efthymios-Spyridon; Lougiakis, Nikolaos; Pouli, Nicole; Marakos, Panagiotis; Skaltsounis, Alexios-Leandros; Nam, Sangkil; Jove, Richard; Horne, David; Gioti, Katerina; Pratsinis, Harris; Kletsas, Dimitris; Tenta, Roxane; Medicinal Chemistry; vol. 13; 4; (2017); p. 365 – 374;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 849068-61-7, 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 849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 1; Methyl 5-bromo-l/7-pyrrolo [2,3-/>] pyridine-3-carboxylate; A solution of 5-bromo-l//-pyrrolo[2,3-6]pyridine (0.200 g, 1.01 mmol; described in: Mazeas,D. et al, Heterocycles 1999, 50, 1065-1080) in dichloromethane (12 mL) was added to asuspension of aluminum chloride (0.704 g, 5.28 mmol) in dichloromethane (5 mL) under anatmosphere of nitrogen. The resulting mixture was stirred at room temperature for 40 min togive a brownish solution. Trichloroacetyl chloride (0.56 mL, 5.0 mmol) was added and themixture was stirred at room temperature for 17 h. Methanol (10 mL) was added and thesolvent was evaporated in vacuo. The residue was treated with aqueous potassium hydroxide(3 M, 10 mL) and methanol (5 mL) and heated at 60 C for 1 h and 15 min. The mixture wasallowed to cool to room temperature and the pH was adjusted to 1-2 using aqueoushydrochloric acid (2 M). The aqueous phase was extracted with ethyl acetate, dried oversodium sulfate, and the solvent was evaporated to give a brown residue. Acetyl chloride (10mL) was added dropwise to cooled methanol (0 C, 20 mL). The resulting solution was addedto a solution of the brown residue in methanol (10 mL) at room temperature, and the resultingmixture was heated at reflux for 3 h. The mixture was allowed to cool to room temperatureand the solvent was evaporated to give a yellow solid. The crude product was purified on asilica gel column using a gradient, ethyl acetate/heptane mixture (10, 20, 30,40, 50% ethylacetate), as the eluent to give 0.165 g (64% yield) of the title compound as a pale pink solid:’H NMR (DMSO-d6, 300 MHz) 5 12.80 (br s, 1 H), 8.41 (s, 2 H), 8.30 (d, J= 3.0 Hz, 1 H),3.83 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) 6 163.9, 147.0, 144.1, 134.5,130.5, 119.6,113.1, 105.0, 51.1; MS (ES) m/z 255 and 257 (M++l).

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 849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; WO2006/1754; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 274-76-0, 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.274-76-0, name is Imidazo[1,2-a]pyridine, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

a) Imidazo [1, 2-a] pyridine-3-carbaldehyde; Imidazo [1, 2-a] pyridine (0.500 g, 4.23 mmol) was dissolved in 1 mL of DMF and phosphorus oxychloride (0.71 g, 4.6 mmol) was added dropwise and the mixture was stirred and checked on LC-MS. After lh the mixture was poured into water and made alkaline with 1M NaOH. The mixture was extracted three times with EtOAc and the combined organic layer was washed with water, dried over Na2SO4, filtered and evaporated. The crude product was flash chromatographed on silica gel with DCM: MeOH 99: 1-96: 4. Yield: 83 mg (13%). ‘H NMR (300 MHz, CDCl3) 6 9.95 (s, 1H), 9.50 (m, 1H), 8.32 (s, 1H), 7.80 (m, 1H), 7.56 (m, 1H), 7.13 (m, 1H).

The chemical industry reduces the impact on the environment during synthesis 274-76-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; WO2005/66132; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 5444-01-9, 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.5444-01-9, name is 4-Methylnicotinonitrile, molecular formula is C7H6N2, molecular weight is 118.1359, as common compound, the synthetic route is as follows.

1M LiHMDS (45mL, 44.794mmol) was added to a solution of 4- methylnicotinonitrile (2.52g, 21.33mmol) in THF (15mL) at -78C and the resulting reaction mass was stirred at -78C for 1 hour. This was followed by the addition of dimethyl carbonate (1.98mL, 23.464mmol) and stirred the resulting reaction mass at – 78C for 1 hour and further at 0C for 2 hours. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mass was quenched with saturated NH4C1 solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (25% ethyl acetate in hexane) afforded 530 mg of the product (14.10% yield).1H NMR (300 MHz, CDC13): delta 8.9 (s, 1H), 8.79 (d, 1H), 7.4 (d, 1H), 3.9 (s, 2H), 3.79 (s, 3H)

The chemical industry reduces the impact on the environment during synthesis 5444-01-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; BOCK, Mark G.; GAUL, Christoph; GUMMADI, Venkateshwar Rao; MOEBITZ, Henrik; SENGUPTA, Saumitra; WO2012/35078; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 88912-24-7, 5,6-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, 88912-24-7, blongs to pyridine-derivatives compound. Recommanded Product: 88912-24-7

Sodium hydride (CAN 7646-69-7, 60% w/w, 1.05 g, 26 mmol) was added tocyclopropylmethanol (CAN 2516-33-8, 7.5 g) at 0C and the mixture was stirred for 1 h. 5,6-Dichloro-pyridine-2-carboxylic acid (1 g, 5 mmol) was added and the mixture was heated to 95C for 3 h. The solvent was removed under reduced pressure. The residue was diluted with water (10 mL) and adjusted to pH = 3.0 by hydrochloric acid (3 N). The solution was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were washed with water (3 x 30 mL) and brine (2 x 40 mL) and evaporated to dryness to give the crude product (0.35 g, 25%>), which was used in the next step without further purification, MS (EI): m/e = 228.1 [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,88912-24-7, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; BISSANTZ, Caterina; GRETHER, Uwe; HEBEISEN, Paul; KIMBARA, Atsushi; LIU, Qingping; NETTEKOVEN, Matthias; PRUNOTTO, Marco; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; ULLMER, Christoph; WANG, Zhiwei; YANG, Wulun; WO2012/168350; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 58819-88-8, 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 58819-88-8 as follows.

To an oven-dried 40 mL vial was added 6-bromo-2-methoxynicotinaldehyde, dichloromethane (0.5M), and (R)-2-methylpropane-2-sulfmamide (1.0 equiv.) at room temperature. To the vial was then added titanium tetraethoxide (2.0 equiv.). The mixture was stirred overnight before being diluted with sodium bicarbonate solution. The contents of the vial were filtered through celite, and the filtrate was washed once with water and once with brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography using hexanes/ethyl acetate gradient to yield (R,E)-N-((6-bromo-2-methoxypyridin-3-yl)methylene)-2-methylpropane-2- sulfmamide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,58819-88-8, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 29681-44-5, Adding some certain compound to certain chemical reactions, such as: 29681-44-5, name is Methyl 5-bromonicotinate,molecular formula is C7H6BrNO2, 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 29681-44-5.

To a solution methyl 5-bromonicotinate (5 g, 23 mmol) in ethanol (40 mL) was added hydrazine hydrate (6 mL, 115 mmol). The reaction mixture was refluxed at 90 C for 4 h. After this time, the reaction mixture was evaporated to dryness and then redissolved in ethyl acetate. The organic layer was washed with water, dried and evaporated to yield 5 -bromonicotinohydrazide (3.4 g, 72 %). LCMS Method T: retention time 0.573 min; [M+l] = 216.0, 218.0.

According to the analysis of related databases, 29681-44-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; JOHNSON, James A.; LLOYD, John; FINLAY, Heather; JIANG, Ji; NEELS, James; DHONDI, Naveen Kumar; GUNAGA, Prashantha; BANERJEE, Abhisek; ADISECHAN, Ashokkumar; WO2011/28741; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 929617-30-1, Adding some certain compound to certain chemical reactions, such as: 929617-30-1, name is 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine,molecular formula is C7H6BrN3, 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 929617-30-1.

To a solution of 5-Bromo-3-methyl-lH-pyrazolo[3,4-c]pyridine from Example 102 (106 mg, 0.5 mmol) in DMF (5 mL) was added Pd(dppf)Cl2 ( 20 mg ), saturated solution of Na2C03 ( 1 mL ) and lH-pyrazol-3-ylboronic acid ( 67 mg, 0.6 mmol ). The mixture was stirred under argon for 16 h at 80 C. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE = 1 : 1) to afford 103 (15 mg, 15% ). 1H NMR (500 MHz, MeOD) delta 8.96 (s, 1H), 8.23 (s, 1H), 7.71 (s, 1H), 6.90 (d, J= 1.5, 1H), 2.65 (s, 3H). ESI MS m/z = 200.1 (M+l)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 929617-30-1, 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; LEE, Wendy; TSUI, Vickie Hsiao-Wei; WANG, Xiaojing; WEN, Zhaoyang; WO2013/24002; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 112110-07-3, 5-(Trifluoromethyl)pyridin-3-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, 112110-07-3, blongs to pyridine-derivatives compound. Formula: C6H5F3N2

A mixture of Pd2(dba)3 (11 mg, 0.012 mmol) and BrettPhos (13 mg, 0.025 mmol) in l,4-dioxane (1 mL) was stirred at 50 C for 10 min. l-(3-chloro-5-methyl-5H-chromeno[4,3- c]pyridin-8-yl)pyrrolidin-2-one (80 mg, 0.25 mmol), 5-(trifluoromethyl)pyridin-3-amine (49 mg, 0.30 mmol) in dioxane (5 mL) and CS2CO3 (248 mg, 0.762 mmol) were added and the resulting mixture was stirred at 100 C for 16 h. A black brown mixture was formed. LCMS (Rt = 0.702 min; MS Calcd: 440.2; MS Found: 440.9 [M+H]+). The reaction mixture was diluted with DCM (10 mL), filtered and concentrated. The residue was purified by prep-HPLC (0.05% NH32O as an additive) and lyophilized to give l-(5-methyl-3-((5- (trifluoromethyl)pyridin-3-yl)amino)-5H-chromeno[4,3-c]pyridin-8-yl)pynOlidin-2-one (25.0 mg, yield: 22%) as a white solid. (1164) NMR (400 MHz, DMSO-r/e) d 1.53 (3H, d, J= 6.8 Hz), 2.00-2.09 (2H, m), 2.52 (2H, overlap with DMSO), 3.83 (2H, t , J= 7.6 Hz), 5.29 (1H, q, J= 6.8 Hz), 6.77 (1H, s), 7.30 (1H, dd, J = 8.4, 2.0 Hz), 7.39 (1H, d, J= 2.0 Hz), 7.91 (1H, d, J= 8.4 Hz), 8.42 (1H, s), 8.74 (1H, s), 9.79 (1H, t, J = 2.0 Hz), 8.94 (1H, d, J= 2.4 Hz), 9.85 (1H, brs).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112110-07-3, its application will become more common.

Reference:
Patent; PETRA PHARMA CORPORATION; KESICKI, Edward A.; LINDSTROeM, Johan; PERSSON, Lars Boukharta; VIKLUND, Jenny; FORSBLOM, Rickard; GINMAN, Tobias; HICKEY, Eugene R.; DAHLGREN, Markus K.; GERASYUTO, Aleksey I.; (391 pag.)WO2019/126730; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 89282-03-1, 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 89282-03-1 as follows.

A reaction mixture containing 3-ethynyl-5-nitro-1 -trityl-1 H-indazole (215 mg, 0.5 mmol), 3-iodo-pyridin-4-ol (132 mg, 0.6 mmol), copper (I) iodide (4.5 mg, 0.025 mmol), PdCI2(PPh3)2 and triethylamine (120 mg, 1.2 mmol) in DMF (3 ml_) was heated at 100 C overnight under argon. After the completion of reaction (shown by TLC), ethyl acetate (50 mL)was added and the reaction mixture was added to water. The organic layer was collected, washed with water, brine and concentrated under vacuum. After purification using silica (7% methanol in dichloromethane), the desired product was obtained (210 mg, 0.4 mmol ) in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89282-03-1, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2008/153858; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem