Category: pyridine-derivatives

Adding a certain compound to certain chemical reactions, such as: 1448427-99-3, 6-(4-Isopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-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, 1448427-99-3, blongs to pyridine-derivatives compound. Formula: C10H13N5

WXBB-14 (1.99 g, 4.39 mmol, 1.00 eq, HCl) (purity 65.50%) was dissolved in anhydrous dichloromethane (25 mL) to form a suspension, and anhydrous N,N-dimethylformamide (20.00 mg, 273.64 mumol, 21.05 muL, 0.06 eq) was added. The system was stirred at 25 C. for 1 hour under N2 condition. The reaction solution was then evaporated on a rotary evaporator to become thick, added with anhydrous dichloromethane (25 mL), evaporated on a rotary evaporator to become thick, repeated three times, then added with anhydrous dichloromethane (25 mL), and added successively with WXBB-8 (1.00 g, 4.92 mmol, 1.12 eq) and diisopropylethylamine (1.14 g, 8.83 mmol, 1.54 mL, 2.01 eq). The system was stirred at 25 C. for 1 hour. The reaction solution was poured into water (100 mL) and extracted with dichloromethane (100 mL*2). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was dried on a rotary evaporator under reduced pressure to obtain a crude product. The crude product was separated and purified with prep-HPLC: Waters Xbridge 150*25 mm 5 mum; mobile phase: [water (10 mM NH4HCO3)-ACN]; B %: 22%-52%, 10 min. WXBB-16 (300.00 mg, 673.42 mumol, 15.33% yield, 100% purity) was obtained as a white solid, 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 0.81-0.87 (m, 2H) 0.87-0.95 (m, 2H) 1.62 (s, 6H) 1.86-1.97 (m, 1H) 2.30 (s, 3H) 5.50 (quin, J=6.71 Hz, 1H) 6.81 (d, J=1.25 Hz, 1H) 7.21 (d, J=12.55 Hz, 1H) 7.46 (d, J=1.25 Hz, 1H) 7.91-7.97 (m, 1H) 8.09 (dd, J=7.65, 2.13 Hz, 2H) 8.38 (s, 1H) 8.41 (d, J=7.78 Hz, 1H) 9.07 (br d, J=15.81 Hz, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1448427-99-3, its application will become more common.

Reference:
Patent; FUJIAN COSUNTER PHARMACEUTICAL CO., LTD.; Wu, Chengde; Yu, Tao; Li, Ning; Chen, Shuhui; US2019/375728; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1211518-35-2, 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.1211518-35-2, name is Methyl 6-chloro-5-(trifluoromethyl)picolinate, molecular formula is C8H5ClF3NO2, molecular weight is 239.58, as common compound, the synthetic route is as follows.

Methyl 6-{1-[(benzyloxy)carbonyl]hydrazino}-5-(trifluoromethyl)pyridine-2-carboxylate Methyl 6-chloro-5-(trifluoromethyl)pyridine-2-carboxylate (3.00 g, 12.5 mmol), benzyl hydrazinecarboxylate (2.29 g, 13.8 mmol) and tris(dibenzylideneacetone)dipalladium (573 mg, 626 mumol) were suspended in toluene (60 ml) under argon. 1,1′-Bis(diphenylphosphino)ferrocene (694 mg, 1.25 mmol) and caesium carbonate (4.90 g, 15.0 mmol) were added and the reaction mixture was stirred at 80 C. for 3 h. The reaction mixture was admixed with water and ethyl acetate, and the organic phase was removed, washed with water and saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated. The residue was purified via column chromatography (silica gel; eluent: cyclohexane/ethyl acetate 9:1, 0:1). The product-containing fractions were concentrated under reduced pressure, and 1.87 g (86% purity, 35% of theory) of the title compound were obtained. LC-MS (Method 1): Rt=1.23 min; MS (ESIneg): m/z=368 [M-H]- 1H-NMR (500 MHz, DMSO-d6) delta[ppm]: -0.007 (1.19), 0.006 (0.87), 1.160 (2.79), 1.174 (5.66), 1.189 (2.80), 1.398 (1.98), 1.988 (10.25), 2.518 (0.42), 3.038 (0.55), 3.051 (0.56), 3.852 (16.00), 4.008 (0.77), 4.022 (2.29), 4.037 (2.24), 4.051 (0.73), 4.484 (1.47), 4.496 (1.51), 4.998 (0.87), 5.036 (1.06), 5.085 (0.93), 5.125 (7.85), 5.134 (1.18), 5.146 (1.34), 5.157 (0.63), 7.107 (0.52), 7.195 (0.84), 7.221 (0.64), 7.232 (0.48), 7.238 (0.48), 7.271 (0.56), 7.287 (0.79), 7.309 (5.08), 7.316 (2.18), 7.319 (2.37), 7.326 (1.95), 7.340 (1.80), 7.364 (2.08), 7.380 (3.95), 7.394 (6.93), 7.409 (1.97), 7.416 (1.42), 7.422 (1.02), 7.482 (1.90), 7.498 (2.13), 7.532 (0.42), 8.085 (2.06), 8.101 (1.89), 8.765 (2.66), 8.849 (0.45), 9.009 (0.47), 9.367 (2.77).

The chemical industry reduces the impact on the environment during synthesis 1211518-35-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; BIBER, Nicole; BROCKSCHNIEDER, Damian; GERICKE, Kersten Matthias; KOeLLING, Florian; LUSTIG, Klemens; MEDING, Joerg; MEIER, Heinrich; NEUBAUER, Thomas; SCHAeFER, Martina; TIMMERMANN, Andreas; ZUBOV, Dmitry; TERJUNG, Carsten; LINDNER, Niels; BADOCK, Volker; MOOSMAYER, Dieter; MIYATAKE ONDOZABAL, Hideki; MOORE, Steven; SCHULZ, Alexander; (458 pag.)US2019/160048; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 99368-68-0 ,Some common heterocyclic compound, 99368-68-0, molecular formula is C6H4ClF3N2, 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.

B. To compound 27a (0.241 g, 1.23 mmol) in 4 mL CH3CN was added iPr2NEt (0.24 mL, 1.38 mmol) and compound 20b (0.24 mL, 1.32 mmol). After 18 hours the reaction was evaporated in vacuo, taken up in 25 mL EtOAc and washed successively with 25 mL saturated NaHCO3 then 25 mL brine. The organic phase was dried over Na2SO4, filtered, and evaporated in vacuo to a residue. The residue was purified via silica gel chromatography (30-60% EtOAc/heptane) to give compound 27b as a yellow-tan powder. MS: M+H+=397.0, 1H NMR (d6-DMSO): delta 10.67 (s, 1H), 8.80 (s, 1H), 8.59 (s, 1H), 7.69 (d, 2H), 7.51 (d, 2H), 3.02 (t, 2H), 2.78 (t, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,99368-68-0, its application will become more common.

Reference:
Patent; Codd, Ellen; Dax, Scott L.; Flores, Christopher; Jetter, Michelle; Youngman, Mark; US2006/223837; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 56826-61-0, 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.56826-61-0, name is (2-Methylpyridine-3-yl)methanol, molecular formula is C7H9NO, molecular weight is 123.1525, as common compound, the synthetic route is as follows.

(a) 2-methyinicotinaidehyde: To a stirred solution of (2-methyipyridin-3-yl)methanoi (200 mg, 1.6 mmol) in CH2CI2 (10 mL) was added Mn02 (200 mg, 2.3 mmol). The mixture wasrefluxed overnight under rutrogcn. The solid was removed by fihration. After removal ofsolvent, the crude product was purified by silica gel column chromotography (petroleumether/EtOAc = i/i) to give the title compound (120 rug, 60%) as a colorless liquid .LCMS-PI:122.0 [M+H]t R = 0.344 miii.

Statistics shows that 56826-61-0 is playing an increasingly important role. we look forward to future research findings about (2-Methylpyridine-3-yl)methanol.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19626; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 866546-09-0, 3-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

To a stirred suspension of NaH (1.4 g, 58.33 mmol) in DMF (30 mL) was added 3-bromo-5-chloro 1H pyrrolo[2,3-b]pyridine 2 (7.0 g, 30.43 mmol) in DMF at 0 C. After 1h, a solution of p-TsCl (6.3 g, 33.47 mmol) in DMF (20 mL) was added slowly at the same temperature and stirred for 2 h. After completion of the reaction (as indicated by TLC), the mixture was poured in to ice cold water (200 mL), filtered the precipitated solid and dried to afford 3-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine 3 (8.5 g, 22.14 mmol, 73 %) as an off-white solid. TLC system: 10% EtOAc in hexane Rf : 0.8 LCMS (ESI): m/z 386.4 [M+H]+

The synthetic route of 866546-09-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina, C.; LEE, Sam SK; FEESE, Michael, David; (206 pag.)WO2020/23813; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 73406-50-5, 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. 73406-50-5, name is Ethyl 3-hydroxypicolinate. A new synthetic method of this compound is introduced below.

The reaction was performed under Ar atmosphere.A solution of ethyl 3-hydroxypicolinate (2.10 g, 12.6 mmol) and ethyl bromoacetate(1.60 mL, 14.4 mmol) in anhydrous acetone (25 mL) was treated with anhydrousK2003,stirred under reflux for 15 h and cooled down to 23 00. The mixture was filteredand the solvent evaporated. The residue was dissolved in CH2CI2 (100 mL), washed with water (3 x 50 mL), dried over anhydrous MgSO4, filtered and evaporated. Column chromatography (SiC2 EtOAc/Heptane 25:75 -> 40:60) gave Ethyl 3-(2-ethoxy-2- oxoethoxy)picolinate (2.42 g, 76%) as a colorless oil.1H NMR (400 MHz, Chloroform-o) 6 = 8.36 (dd, J= 4.5, 1.2 Hz, 1H, H-Ar), 7.39 (dd, J8.5, 4.5 Hz, 1H, H-Ar), 7.29 (dd, J= 8.6, 1.2 Hz, 1H, H-Ar), 4.74 (s, 2H, O-CH2C=O),4.47 (q, J= 7.1 Hz, 2H, O-CH2CH3), 4.27 (q, J= 7.1 Hz, 2H, O-CH2CH3), 1.44 (t, J=7.1 Hz, 3H, O-CH2CH3), 1.29 (t, J= 7.1 Hz, 3H, O-CH2CH3) ppm.MS (ESl+, H20/MeCN) mlz(%): 254.0 (100, [M + H]j.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73406-50-5, Ethyl 3-hydroxypicolinate, and friends who are interested can also refer to it.

Reference:
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; WILL, David William; REID, George; CHARAPITSA, Iryna; LEWIS, Joe David; (187 pag.)WO2018/229193; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 81803-60-3 , The common heterocyclic compound, 81803-60-3, name is Ethyl imidazo[1,5-a]pyridine-3-carboxylate, molecular formula is C10H10N2O2, 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.

Ethyl imidazo[1 ,5-a]pyridine-3-carboxylate (25 mg, 0.13 mmol), (f?)-1-(2-fluorophenyl)- 4,5,6,7-tetrahydro-1 H-indazol-4-amine hydrochloride (S15) (49 mg, 0.18 mmol) and bis(trimethylaluminum)-1 ,4-diazabicyclo[2.2.2]octane adduct (51 mg, 0.20 mmol) were dissolved in THF (2 ml). The reaction mixture was stirred at 60C for 5 h under nitrogen atmosphere. The solvent was removed at reduced pressure and DCM and brine were added. The phases were separated and the organic phase was filtered and concentrated. The mixture was purified by column chromatography eluting with a gradient of EtOAc in hexanes (20-70%) to give the title compound, 31 mg (62%). 1H NMR (400 MHz, CDCI3) delta 9.54 (d, J = 8.2 Hz, 1 H), 7.71 (s, 1 H), 7.57 (d, J = 9.1 Hz, 1 H), 7.53 (d, J = 7.7 Hz, 1 H), 7.48 (td, J = 7.7, 1.7 Hz, 1 H), 7.45 (d, J = 0.7 Hz, 1 H), 7.44-7.37 (m, 1 H), 7.30-7.20 (m, 2H, overlapping with the solvent peak), 6.98 (ddd, J = 9.1 , 6.6, 1.0 Hz, 1 H), 6.85 (ddd, J = 7.2, 6.6, 1.3 Hz, 1 H), 5.43-5.32 (m, 1 H), 2.68-2.49 (m, 2H), 2.22-2.09 (m, 1 H), 2.03-1.82 (m, 3H). m/z (ES+) 376 [M+H]+.

The synthetic route of 81803-60-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LAIN, Sonia; DRUMMOND, Catherine; LEEUWEN, Ingeborg van; HARALDSSON, Martin; JOHANSSON, Lars; SANDBERG, Lars; YNGVE, Ulrika; (126 pag.)WO2017/77280; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26163-03-1, 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 26163-03-1, name is 3-Bromo-5-chloropyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-bromo-5-chloro-2-pyridinamine (5.0 g), bromoacetoaldehyde diethyl acetal (7.3 mL), p-toluenesulfonic acid monohydrate (498 mg) and ethanol (20 mL) was stirred at 80 C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated to give a residue. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give a residue. The obtained residue was washed with ethyl acetate/IPE to give the title compound (4.71 g). (1141) 1H NMR (300 MHz, DMSO-d6) delta 7.68 (1H, d, J=1.2 Hz), 7.75 (1H, d, J=1.8 Hz), 8.06 (1H, d, J=1.2 Hz), 8.91 (1H, d, J=1.8 Hz).

According to the analysis of related databases, 26163-03-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; FUJIMOTO, Jun; LIU, Xin; KURASAWA, Osamu; TAKAGI, Terufumi; CARY, Douglas Robert; BANNO, Hiroshi; ASANO, Yasutomi; KOJIMA, Takuto; (159 pag.)US2019/169166; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1450634-01-1, 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 1450634-01-1 as follows.

To a solution of 3-(prop-1-en-2-yl)picolinonitrile in acetic acid was added 10% Pd/C. The parr shaker bottle was evacuated/H2 purged 3x, and then shaken at Sopsi until starting material was consumed (typically Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore; JIANG, Rong; SONG, Xinyi; WO2013/119639; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 51173-05-8, 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. 51173-05-8, name is 5-Fluoro-2-hydroxypyridine. A new synthetic method of this compound is introduced below.

The solid from above containing (4-80) was divided in 4 batches and treated with H2SO4 and fuming HNO3 as shown below. The amounts used were: Compound 4-80 was dissolved in sulfuric acid (the larger amounts indicated above) at rt and then heated to 65 C. A preformed solution of fuming nitric acid and sulfuric acid (the smaller amount indicated above) was added dropwise. The temperature was kept between 65 C. and 80 C. (rxn is exothermic and although the bath is at 65 C., temperature goes higher, usually 75, sometimes 80 C.). After the addition was complete, the reaction mixture was heated at 65 C. for an additional hr. The reaction mixture was then cooled to rt and poured in a flask containing ice) (20 g of ice/gr compound, evolution of gas occurred). A solid precipitated out and it was collected by filtration (1HNM? showed 4-80 and something else (discarded)). [1493] The aqueous layer was extracted with AcOEt several times (3-5) and concentrated on a rotary evaporator under vacuum to afford a solid that was triturated with ether to afford 5-80 as a bright yellow solid. A total of 117 g of desired product was collected in the first crop (27% yield from diazonium salt). A portion did not crystallize: this oil was triturated with MeOH and Et2O to afford 3.6 g of 5-80; another precipitation from the mother liquid afforded an additional 6.23 g of the desired product 5-80 [1494] Total:117.0+3.6+6.23 =126.83. 30.4%). Yield for 3 steps (decomposition of diazonium salt; deprotection and nitration). [1495] Analytical data from Notebook: 53877-115: 1HNMR(delta, MeOD): 8.56-8.27 (dd, J=7.5, 3.3 Hz, 1H), 8.01 (d, J=3.3 Hz, 1H); LC/MS(M+1)+=158.9; rt=0.15 min. [1496] Note: A portion of the aqueous acidic solution was taken and neutralized with Na2CO3 until effervescence stopped and then it was extracted with AcOEtA different product was obtained. No desired product in these extracts.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,51173-05-8, 5-Fluoro-2-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Wang, Tao; Zhang, Zhongxing; Meanwell, Nicholas A.; Kadow, John F.; Yin, Zhiwei; Xue, Qiufen May; Regueiro-Ren, Alicia; Matiskella, John D.; Ueda, Yasutsugu; US2004/110785; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem