Day: January 26, 2021

Reference of 20265-35-4, 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.20265-35-4, name is 2-Methoxy-3-nitropyridine, molecular formula is C6H6N2O3, molecular weight is 154.12, as common compound, the synthetic route is as follows.

EXAMPLE 13 Synthesis of 2-methoxy-3-aminopyridine STR28 To a solution of the compound of Example 12 (17.12 g, 0.11 mol) in ethanol (180 mL) in a Parr bottle, was added 4percent Pd/C (3.43 g). The bottle was sealed, purged with nitrogen and was pressurized (5 psi) with hydrogen. After stirring at room temperature for 2 hr, the reaction vessel was vented, purged with nitrogen and filtered. The clear filtrate was concentrated to give the title compound (15.3 g, 90percent). 1 H NMR (CDCl3): 7.58 (dd, J=5, 2 Hz, 1H); 6.87 (dd, J=8, 2 Hz, 1H); 6.72 (dd, J=8, 5 Hz, 1H); 3.98 (s, 3H).

Statistics shows that 20265-35-4 is playing an increasingly important role. we look forward to future research findings about 2-Methoxy-3-nitropyridine.

Reference:
Patent; C.D. Searle & Co.; US5652363; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 89793-09-9, 2-Chloro-4,6-dimethyl-3-nitropyridine, 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, 89793-09-9, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a solution of 2-chloro-4,6-dimethyl-3-nitropyridine (17.9 g, 96 mmol) and methyl 3-(4-aminophenyl)propanoate (19 g, 96 nmol) in DMSO (100 mL) was added N,N-diisopropylethylamine (26 g, 200 mmol), and the reaction mixture was heated at 140 C. overnight. The reaction mixture was partitioned between water (400 mL) and ethyl acetate/toluene (v/v, 2:1, 300 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate/toluene (v/v, 2:1, 200 mL). The combined organic extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated. To a solution of residual oil in methanol (100 mL) was added 2 N aqueous NaOH (150 mL, 300 mmol) and the resulting mixture was stirred at room temperature for 2 h. The volatile component was removed under reduced pressure and the residue was washed with ethyl acetate (200 mL). The aqueous phase was acidified with 2N hydrochloric acid (200 mL, 400 mmol) and extracted with ethyl acetate (3¡Á200 mL). The extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated to give 23.2 g (77%) of the title compound as pale brown solids[1898] 1H-NMR (CDCl3) delta: 9.57 (1H, s), 7.56 (2H, d, J=8.4 Hz), 7.19 (2H, d, J=8.4 Hz), 6.52 (1H, s), 2.95 (2H, t, J=7.5 Hz), 2.66 (2H, t, J=7.5 Hz), 2.55 (3H, s), 2.43 (3H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,89793-09-9, its application will become more common.

Reference:
Patent; Shimojo, Masato; Taniguchi, Kana; US2003/236260; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 75418-74-5, 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. 75418-74-5, name is Methyl 3-oxo-3-(pyridin-2-yl)propanoate, molecular formula is C9H9NO3, 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 2: 5-Pyridin-2-ylthieno[3,2-b]pyridin-7-ol; 3-Thienylamine oxylate (5.55 g, 30 mmol, 1.0 equiv) and methyl 3-oxo-3-pyridin-2- ylpropanoate (5.67 g, 30 mmol, 1.0 equiv) were combined in a round bottom flask equipped with a Dean Stark reflux condenser and taken up in anhydrous toluene (100 mL). 4N HCI in 1 ,4-dioxane (0.733 mL, 3 mmol, 0.10 equiv) was added and the reaction mixture was refluxed for 12 h. The crude product was filtered and the black solids were taken on without further purification (6.02 g, 90% yield): 1H NMR (400 MHz, DMSO-d6) delta 8.79 (d, J = 4.5Hz, 1 H), 8.26 (d, J = 8.1Hz, 1 H), 8.01-7.97 (m, 1 H), 7.92 (d, J = 5.3Hz, 1 H), 7.53 (dd J = 7.2, 4.9Hz, 1H), 7.07(s, 1H), 7.05 (d, J = 5.3Hz, 1 H); LCMS (ESI+) for C12H8N2OS m/z 229 (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 75418-74-5, Methyl 3-oxo-3-(pyridin-2-yl)propanoate.

Reference:
Patent; PFIZER INC.; WO2006/43145; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13534-98-0, 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. 13534-98-0, name is 4-Amino-3-bromopyridine. A new synthetic method of this compound is introduced below.

3-Bromo-5-iodopyridin-4-amine A solution of potassium iodide (2.88 g, 17.34 mmol) and iodine (2.75 g, 10.84 mmol) in water (21 mL) was added dropwise to a solution of 4-amino-3-bromopyridine (2.5 g, 14.45 mmol) and sodium carbonate (0.919 g, 8.67 mmol) in water (10 mL) and the mixture was stirred at reflux for 20 h. The mixture was diluted with water and EtOAc and the layers were separated. The organic layer was extracted with EtOAc three times. The combined organic layers were washed with sat. Na2S2O3 three times, dried over MgSO4, filtered off and the filtrate concentrated in vacuum. The resulting brown oil was purified by chromatography on silica gel (biotage, CyHex/EtOAc, 50:50 to 0:100) to give product (951 mg, 22%) and starting material (1.66 g) as light yellow solids.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13534-98-0, 4-Amino-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, 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 tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, blongs to pyridine-derivatives compound. Application In Synthesis of tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate

4-(6-Amino-pyridin-3-yl)-piperazine-1 -carboxylic acid fe/t-butyl ester (2.50 g, 8.98 mmol) in DCM (30 mL) and 4M HCI in 1 ,4-dioxane (1 1.2 mL, 44.9 mmol) is stirred for 16 h at rt. The reaction mixture is filtered and washed with ether to give the title compound. (0452) Yield: 2.23 g (99%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,571188-59-5, tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HYDRA BIOSCIENCES, INC.; BOUYSSOU, Thierry; GOTTSCHLING, Dirk; HEINE, Niklas; SMITH KEENAN, Lana Louise; LOWE, Michael D.; RAZAVI, Hossein; SARKO, Christopher Ronald; SURPRENANT, Simon; TAKAHASHI, Hidenori; TURNER, Michael Robert; WU, Xinyuan; (182 pag.)WO2019/81637; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 144100-07-2 , The common heterocyclic compound, 144100-07-2, name is 2-Bromo-6-fluoropyridine, molecular formula is C5H3BrFN, 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.

a) Under inert gas atmosphere 28.4 mL (56.8 mmol) of a sodium-bis-(trimethylsilyl)-amide solution in THF (c=2 mol/L) are chilled to ?17¡ã C. and dropwise charged with 2.00 g (11.3 mmol) 2-bromo-6-fluoropyridine. Afterwards 2.14 g (22.7 mmol) dimethyl sulfone are added and the reaction mixture is stirred at ?17¡ã C. for 1 h. The reaction is quenched by the addition of aq. sat.NaCl solution and extracted with EtOAc. The organic layer is dried over MgSO4, filtered and the solvent is removed in vacuo. [0496] C7H8BrN2O2S (M=250.1 g/mol) [0497] ESI-MS: 250/252 [M+H]+

The synthetic route of 144100-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FLECK, Martin; HEINE, Niklas; NOSSE, Bernd; ROTH, Gerald Juergen; US2014/213568; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.903522-29-2, name is 3,5-Difluoroisonicotinic acid, molecular formula is C6H3F2NO2, molecular weight is 159.09, as common compound, the synthetic route is as follows.Recommanded Product: 903522-29-2

General procedure: DMF (10 mg, 0.137 mmol) was added to a mixture of 3-fluoropicolinic acid (162 mg, 1.15 mmol) in anhydrous CH2Cl2 (3 mL). The mixture was cooled in an ice bath and then treated with oxalyl chloride (0.1 mL, 1.14 mmol) dropwise. The reaction mixture was warmed to r.t. overnight. A mixture of 3-chloro-N1-methyl-4-nitrobenzene-1,2-diamine (Intermediate 2, 208 mg, 1.03 mmol) and triethylamine (0.16 mL, 1.15 mmol) in anhydrous CH2Cl2 (3 mL) was then added, and the mixture was stirred at r.t. for 2 hrs. The solvent was concentrated under vacuum, and the residue was dissolved in DMSO (2 mL) and stirred at 60 C. for 3 hrs. After cooling to r.t., water was added and the solid precipitate was collected via filtration, washed with water, and air dried. The crude product obtained was used directly in the next step without further purification.; This compound was prepared according to a modified procedure described for Intermediate 3, using 3,5-difluoroisonicotinic acid instead of 3-fluoropicolinic acid as starting material. Following the addition of DMSO, concentrated HCl (1 mL) was added and the mixture was stirred at 80 C. for 3 hrs. LCMS calculated for C13H8ClF2N4O2 (M+H)+: m/z=325.0; Found: 324.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,903522-29-2, 3,5-Difluoroisonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Nguyen, Minh; Sokolsky, Alexander; Vechorkin, Oleg; Ye, Qinda; Yao, Wenqing; (72 pag.)US2019/315717; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 188637-63-0, Adding some certain compound to certain chemical reactions, such as: 188637-63-0, name is (6-Bromopyridin-2-yl)methanamine,molecular formula is C6H7BrN2, 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 188637-63-0.

To an ice-cold solution of (R)-1-(tert-butoxycarbonyl)piperidine-3- carboxylic acid (1.09g, 4.75mmol) in 50 mL of CH2Cl2, 1-chloro-N,N,2-trimethyl-1- propenylamine (0.69mL, 5.3mmol) was added dropwise with stirring. The stirring was continued for 2 h at this temperature, then (6-bromopyridin-2-yl)methanamine (750 mg, 4.0mmol) was added, followed by 1.6 mL of iPr2NEt. The cooling bath was removed and the reaction mixture was stirred overnight at rt. After completion of the reaction monitored by HPLC, the reaction mixture was added to water (120 mL) and extracted with DCM (2 120 mL). The organic layer was washed successively with an aqueous solution of NaHCO3 (20 mL), water (20 mL), and brine (20 mL), then dried over Na2SO4 and concentrated under reduced pressure. The remaining residue was purified by flash column chromatography (ISCO eluted with Hexanes/EtOAC) to give 1.10g of desire title compound.

According to the analysis of related databases, 188637-63-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (508 pag.)WO2017/35409; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53937-02-3, 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. 53937-02-3, name is 4-Benzyloxy-2-(1H)-pyridone. A new synthetic method of this compound is introduced below.

tert-Butyl 2-bromo-9-methyl-5,7,8,9-tetrahydro-6H-pyrido[3′,4′:4,5]pyrrolo[2,3-b]pyridine-6-carboxylate (0.73 g, 2.0 mmol), 4-benzyloxy pyridinone (0.44 g, 2.2 mmol), and Cs2CO3 (0.72 g, 2.2 mmol) were suspended in DMSO (12 mL), and the air was removed under vacuum for 15 min. The system was flushed with Ar, and 8-hydroxyquinoline (87 mg, 0.60 mmol) and copper iodide (0.49 g, 2.6 mmol) were added to the suspension. The evacuation/Ar flushing process was repeated twice more, and the reaction mixture was heated at 130 C. for 18 h under N2. The mixture was cooled, diluted with 5.0:3.5:1.5 NH4Cl(aq.)/NH4OH/H2O (70 mL), and the resulting suspension was stirred at ambient temperature for 30 min. The resulting solids were collected by filtration, dissolved in CH2Cl2 (30 mL) and washed with 5.0:3.5:1.5 NH4Cl(aq.)/NH4OH/H2O (2*30 mL). The resulting organic solution was dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure. Flash chromatography (40 g ISCO column, (1:1 hexanes/EtOAc)/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 2 column volumes, increased to 50:50 over 12 column volumes and held for 5 column volumes; increased to 0:100 over 10 column volumes and held for 5 column volumes) gave the title compound (0.51 g, 52%) as a yellow foam: 1H NMR (500 MHz, DMSO-d6) delta 8.00 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 7.50-7.36 (m, 5H), 7.29 (d, J=8.0 Hz, 1H), 6.15 (dd, J=8.0, 2.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 5.16 (s, 2H), 4.57 (s, 2H), 3.75 (t, J=5.5 Hz, 2H) 3.67 (s, 3H), 2.88 (t, J=5.5 Hz, 2H), 1.42 (s, 9H); ESI MS m/z 487 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53937-02-3, 4-Benzyloxy-2-(1H)-pyridone, and friends who are interested can also refer to it.

Reference:
Patent; ALBANY MOLECULAR RESEARCH, INC.; US2012/157460; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 80194-68-9, 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 80194-68-9, name is 3-Chloro-5-(trifluoromethyl)picolinic acid. This compound has unique chemical properties. The synthetic route is as follows.

General procedure: General procedure for preparing intermediates 3. As shown in scheme 1, to a solution of 3-chloro-5-(trifluoromethyl)picolinicacid 1 (0.5 g, 2.22 mmol) in 5 mL ofacetonitrile, pyridine (0.7 g, 8.87 mmol) and methanesulphonyl chloride (0.51 g,4.43 mmol) was slowly added at -5 0C, and was left to stir at -5 0Cfor 10 min. The corresponding substituted 2-amino-benzoic acid (2.22 mmol) wasadded and left to stir for further 10 min. Pyridine (0.7 g, 8.87 mmol) and methanesulphonylchloride (0.51 g, 4.43 mmol) were slowly added again below 0 0C. Theresulting mixture was stirred at room temperature for 10 h and monitored byTLC. After the completion of reaction above, water (5 mL) was added to themixture to afford a crystalline solid (intermediate 3) via filter and recrystallization from ethanol.

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 80194-68-9, 3-Chloro-5-(trifluoromethyl)picolinic acid.

Reference:
Article; Luo, Dexia; Guo, Shengxin; He, Feng; Wang, Heying; Xu, Fangzhou; Dai, Ali; Zhang, Renfeng; Wu, Jian; Bioorganic and Medicinal Chemistry Letters; vol. 30; 3; (2020);,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem