Category: pyridine-derivatives

Electric Literature of 1111637-94-5, Adding some certain compound to certain chemical reactions, such as: 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine,molecular formula is C8H7BrN2, 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 1111637-94-5.

Preparation of 3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrolo[2,3-b]pyridine (B-5-5)To a solution of 5-bromo-3-methyl-1 H-pyrrolo[2,3-b]pyridine (B-5-4) (0.5 g, 2.37 mmol) in DMF (150 mL) were added KOAc (0.7 g, 7.11 mmol) and bis(pinacolato)diboron (0.72 g, 2.84 mmol). The resulting mixture was degassed under N2 for 2 minutes. Then Pd(PPh3J2CI2 (0.2 g, 0.237 mmol) was added and the mixture was degassed again. The reaction was heated to 80-900C and stirred overnight. The mixture was poured into water (30 mL), extracted with EtOAc (15 mLchi3). The organic layer was washed with saturated aqueous NaCI, dried over Na2SO4 and concentrated to give crude 3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrrolo[2,3-b]pyridine (B-5-5) (0.7 g), which was used directly in next step.

According to the analysis of related databases, 1111637-94-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116355-18-1, Adding some certain compound to certain chemical reactions, such as: 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine,molecular formula is C8H7BrN2, 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 116355-18-1.

To a solution of 6-bromo-7-methylimidazo(1,2-a)pyridine (9 g, 43.0 mmol) and anhydrous sodium acetate (9.52 g, 116.1 mmol) in MeOH (100 mL) at 0 C. was added iodine (12.0 g, 47.3 mmol). The reaction mixture was stirred at rt for 20 h. The precipitate was collected by filtration and washed with MeOH to afford 6-bromo-3-iodo-7-methylimidazo[1,2-a]pyridine (6 g, 41%) as a light grey solid. 1H NMR (400 MHz, CDCl3) delta 8.30 (s, 1H), 7.64 (s, 1H) 7.49 (s, 1H) 2.50 (s, 3H); MS (ESI) m/z 336.7 [M+H]+.

According to the analysis of related databases, 116355-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62150-47-4, 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.62150-47-4, name is Ethyl 4-bromopicolinate, molecular formula is C8H8BrNO2, molecular weight is 230.06, as common compound, the synthetic route is as follows.

The second step: 8.5 kg of A was added to 35 liters of ammonia water in batches, methane was stirred overnight, and centrifuged to obtain a crude product which was washed with ethyl acetate and centrifuged to obtain 4.5 kg of amide;

Statistics shows that 62150-47-4 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-bromopicolinate.

Reference:
Patent; Chengdu Tong Chuangyuan Pharmaceutical Technology Co., Ltd.; Shou Yuehan; (12 pag.)CN105153023; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 20511-12-0, Adding some certain compound to certain chemical reactions, such as: 20511-12-0, name is 5-Iodopyridin-2-amine,molecular formula is C5H5IN2, 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 20511-12-0.

Step 13-Bromo-5-iodopyridin-2-amine Procedure:To a stirred solution of 5-iodopyridin-2-amine (25.0 g, 113 mmol) in acetonitrile (500 mL) was added NBS (20.2 g, 113 mmol) slowly at room temperature. After the addition, the reaction mixture was stirred at room temperature for a further 72 h. The solvent was evaporated at 40 C. at reduced pressure and the residue was purified by column chromatography (silica gel, 200-300 mesh, ethyl acetate/petroleum ether 3:1, v/v) to give 3-bromo-5-iodopyridin-2-amine (15.9 g, 47%) as a yellow solid. 1H NMR (300 MHz, DMSO): delta 8.07 (s, 1H), 7.98-7.97 (m, 1H), 6.43 (brs, 1H). LC/MS: 298.9 [M+H]+.

According to the analysis of related databases, 20511-12-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hermann, Johannes Cornelius; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/309746; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 76006-11-6, name is 7-Chloro-1H-pyrazolo[3,4-c]pyridine. A new synthetic method of this compound is introduced below., Recommanded Product: 7-Chloro-1H-pyrazolo[3,4-c]pyridine

Trimethylaluminum (23.9 mL, 47.8 mmol, 2M sol. in toluene) was added to a vigorously stirred solution of 7-chloro-1 H-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1.38 g, 1.19 mmol) in THF (109 mL) under argon. The reaction mixture was stirred at 65C for 16 h. The mixture was cooled to RT and poured into sat. aq. NH4CI. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3x). The combined organic extracts were washed with brine then dried (Phase separator) and concentrated under reduced pressure to give 7-methyl-1 H- pyrazolo[3,4-c]pyridine as a solid. MS (LC-MS): 134 [M+H]+, tR (HPLC conditions k): 0.25 min.

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, 76006-11-6, 7-Chloro-1H-pyrazolo[3,4-c]pyridine.

Reference:
Patent; NOVARTIS AG; ALTMANN, Eva; HOMMEL, Ulrich; LORTHIOIS, Edwige Liliane Jeanne; MAIBAUM, Juergen Klaus; OSTERMANN, Nils; QUANCARD, Jean; RANDL, Stefan Andreas; SIMIC, Oliver; VULPETTI, Anna; ROGEL, Olivier; WO2012/93101; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1122-61-8, 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 1122-61-8 as follows.

Example 15 4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25 C. After completion of the addition, the resulting mixture was at 25 C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1122-61-8, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5648496; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 17322-91-7, 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. 17322-91-7, name is 1H-Pyrrolo[3,2-b]pyridin-5(4H)-one. A new synthetic method of this compound is introduced below.

Dissolve 5-hydroxy-1H-pyrrole[3,2]pyridine (10 mmol) in 40 ml of dichloromethane and add 10 ml to it.Triethylamine, controlled temperature below 10 C, adding 2-chloroacetyl chloride (12 mmol) in dichloromethane to the system, adding dropwiseAfter completion, return to room temperature, stir at room temperature for 10 hours, then wash the reaction system with 50 ml of 5% aqueous sodium carbonate solution, organic phase.After drying with anhydrous Na 2 SO 4 and evaporating the solvent, the obtained solid was separated by flash column chromatography.1.9 g pale yellow 2-chloro-1-(5-Hydroxy-1H-pyrrole[3,2]pyridin-1-yl)-ethanone solid, yield 90%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,17322-91-7, its application will become more common.

Reference:
Patent; Sang Qi; (10 pag.)CN108383838; (2018); A;,
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. 1057682-05-9, name is (R)-6-(3-Methylpiperazin-1-yl)nicotinonitrile, molecular formula is C11H14N4, 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. HPLC of Formula: C11H14N4

To a stirred solution of 3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoic acid (5.0 g, 21.19mmol, obtained from Example 29, step 3) in dry DMF (40 mL, -8 vol), 6-[(3R)-3-methylpiperazine-1-yl]-pyridine-3-carbonitrile ( 4.06 g, 20 mmol), EDClHCl (6.08 g, 31.6 mmol),HOBt (3.43 g, 25.4 mmol) and DIPEA (14.5 mL, 84.5 mol) were added at 10-15C andstirred for 22 h. The reaction mixture was quenched with ice cold water (500 mL) andextracted with EtOAc (3 x 70 mL). The combined organic layers were dried over anhydrousNa2S04 and concentrated under reduced pressure to get crude compound. Crude compoundwas stirred with EtOAc (50 mL) for 1 hour at RT, filtered and suck dried. Solid obtained wasagain made slurry with EtOAc. Filtered the solid and washed with EtOAc (50 mL) to afford(50 mL) 6-[(3R)-4-[3-(6-fluoro-4-oxo-3H-quinazolin-2-yl)propanoyl]-3-methyl-piperazin-1-yl]pyridine-3-carbonitrile in 43% yield (3.8g). Chiral HPLC was used to confirm that thecompound is the enantiomer of compound 29. Column used: Lux,5 micron, Cellulose-4 (250X 4.6 mm , 5 micron , Mobile phase: 50:50 n-hexane:(0.1% HCOOH in 1:1ethanol:methanol), Flow rate: 1.0 mL/min, Temperature: 25C. Retention time for Renantiomer= 12.9 min; Retention time for compound 29 = 13.4 min.

With the rapid development of chemical substances, we look forward to future research findings about 1057682-05-9.

Reference:
Patent; MITOBRIDGE, INC.; TAKAHASHI, Taisuke; KLUGE, Arthur; LAGU, Bharat; JI, Nan; (162 pag.)WO2018/125961; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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.

General procedure: To each reaction tube in a 24-position Bohdan MiniBlock XT was added the appropriate aldehyde (5.0 equiv, 1.15 mmol), which was dissolved in MeCN (1 mL). A solution of 2-(benzo[d][1,3]dioxol-5- yl)pyrimidin-4-amine (8) in MeCN (0.13 M, 1.8 mL, 0.23 mmol, 1.0 equiv) was then dispensed into each tube. ClTi(Oi-Pr)3 (95%, 0.35 mL, 1.38 mmol, 6.0 equiv) was added to each tube, followed by AcOH (3 drops). The reactions were shaken at 450 rpm for 5 minutes, and then solid NaBH(OAc)3 (95%, 257 mg, 1.15 mmol, 5.0 equiv) was added to each tube. The reactions were shaken at 450 rpm for an additional 1.5 hours, and then a solution of 15% aqueous NH4OH (2 mL) and CH2Cl2 (2 mL) were added to each tube causing white solids to precipitate. Shaking was continued for 30 minutes at 450 rpm. Using stackable 24-position Bohdan MiniBlock XTs, the liquid portions of the crude reaction mixtures were passed into phase separators, to which H2O (2 mL) was added. The biphasic mixtures were mixed by hand using pipettes, and then the heavier organic layers were passed from the phase separators into new reaction tubes. The white solids in the original reaction tubes were washed with CH2Cl2 (2 mL) and the washings were passed into the closed phase separators. The biphasic mixtures were again mixed by hand using pipettes and the heavier organic layers were passed into the reaction tubes containing the organic layers from the first separation. The crude reaction mixtures were then placed on a sample concentrator to remove the solvents. TFA/MeOH (1:19, 3 mL) was added to each crude reaction mixture, and the samples were then shaken at 450 rpm for 1 hour. The solutions were then passed onto columns of Dowex 50WX4-400 ion exchange resin (2.0 g, pre-washed with TFA/MeOH (1:99, 5 mL)). Each reaction tube was washed with MeOH (2 mL) and the washings were allowed to pass onto the Dowex columns. The columns were washed with MeOH (3 mL) and the washings discarded. The products were then eluted into collection tubes using a mixture of Et3N/MeOH (1:9, 10 mL). Solvents were removed using a sample concentrator and the products were subjected to reverse-phase preparative HPLC purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Article; Coombs, Thomas C.; Tanega, Cordelle; Shen, Min; Wang, Jenna L.; Auld, Douglas S.; Gerritz, Samuel W.; Schoenen, Frank J.; Thomas, Craig J.; Aube, Jeffrey; Bioorganic and Medicinal Chemistry Letters; vol. 23; 12; (2013); p. 3654 – 3661;,
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. 89510-90-7, name is 2-Chloro-5-fluoro-4-pyridinamine, molecular formula is C5H4ClFN2, 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. Product Details of 89510-90-7

To a solution of 2-chloro-5-fluoropyridin-4-amine (1.0 g, 6.82 mmol) in DCM (50 mL) at 0 C was addded TEA (1.046 mL, 7.51 mmol), DMAP (0.083 g, 0.682 mmol) and Boc2O (1.584 mL, 6.82 mmol). The reaction mixture was stirred at room temperature for18 h. The reaction mixture was evaporated under reduced pressure to afford crude product as a black residue. The crude product was purified by silica gel chromatography (eluted with 10% ethyl acetate in petroleum ether) to yield tert-butyl (2-chloro-5-fluoropyridin-4- yl)carbamate 79A (1.0 g, 59.4%). LCMS m/z 247.0 (M+H); rt 0.95 mm; Conditions H.

With the rapid development of chemical substances, we look forward to future research findings about 89510-90-7.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARIKRISHNAN, Lalgudi S.; FINK, Brian E.; BORZILLERI, Robert M.; TONUKUNURU, Gopikishan; RAHAMAN, Hasibur; WARRIER, Jayakumar Sankara; SESHADRI, Balaji; (411 pag.)WO2017/15425; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem