Day: April 21, 2022

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

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

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 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

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 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

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

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. 920979-05-1, name is 5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below., Quality Control of 5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid

23.3 ethyl 5-(trifluoromethyl)pyrrolo[3,2-b]pyridine-2-carboxylate 1 ml (18.71 mmol) of concentrated sulphuric acid is added to a solution of 0.2 g (0.87 mmol) of 5-trifluoromethyl-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid, obtained in step 23.2, in 10 ml of ethanol. The solution is stirred at reflux for 20 hours and then cooled and concentrated under reduced pressure. The resultant residue is subsequently taken up with 50 ml of dichloromethane and then washed successively with 20 ml of a saturated aqueous solution of sodium hydrogen carbonate, 40 ml of water and 20 ml of a saturated aqueous solution of sodium chloride, dried over sodium sulphate and then concentrated under reduced pressure. 0.19 g of product is obtained, which product is used as it is in the subsequent step.

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, 920979-05-1, 5-(Trifluoromethyl)-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid.

Reference:
Patent; SANOFI-AVENTIS; US2009/42873; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 176526-00-4, Adding some certain compound to certain chemical reactions, such as: 176526-00-4, name is 2-(Pyridin-4-yl)benzaldehyde,molecular formula is C12H9NO, 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 176526-00-4.

A solution of tetrabutylammonium fluoride (0.027 ml; 1.0 M in tetrahydrofuran) was added to a solution of 2-pyridin-4-yl-benzoAldehyde (500 mg, 2.73 mmol) and trifluoromethyltrimethylsilane (TMSCF3) (485 mul, 3.28 mmol) in 5 ml of THFin. The resulting mixture was warmed to room temperature and stirred at room temperature for 4 hours. The reaction mixture was then washed with 5 ml of 1N HClAnd stirred overnight at room temperature. The solvent was evaporated to dryness, 9 ml of a 1 M aqueous solution of sodium carbonate was added and the aqueous phase was extracted with chloroform (3 x10 ml), the combined chloroform layers were washed with water and dried over MgSO4. Evaporation of the organic solvent gave 300 mg of 2,2,2-trifluoro-l- (2-Pyridin-4-yl-phenyl) ethanol in a yield of 43%.

According to the analysis of related databases, 176526-00-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laixiken Pharmaceutical Co., Ltd.; A Luojiyasami·dewasajiayalayi; Jin Haihong; Shi Zhicai; A Xiaoke·tunuli; Wang Ying; Zhang Chengmin; (63 pag.)CN104045626; (2017); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16744-81-3, name is 4-Methoxypicolinaldehyde, the common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Methoxypicolinaldehyde

To a cooled (0 °C) solution of 18 (93 mg, 0.67 mmol) and 21 (77 mg, 0.56 mmol) in dry dichloromethane (1 mL) was added NaBH(OAc)3 (178 mg, 0.84 mmol). The reaction mixture was stirred at rt for 6 hr. The reaction was quenched with water, the mixture was diluted with sat. NaHCO3, and then extracted with CHCl3. The extracts were dried over MgSO4 and concentrated by evaporation to give the crude product. To a solution of the product in dry CH2Cl2 (1 mL) was added dropwise the solution of Boc2O (292 mg, 1.34 mmol) in dry CH2Cl2 (2.0 mL). The reaction mixture was stirred at rt overnight. After dilution with sat. NaHCO3, the mixture was extracted with CHCl3. The extracts were dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on SiO2 (CH3Cl :MeOH : NH3 = 100 : 1 : 0.1 ? 40 : 0.1) to give 22 (156 mg, 78 percent) as a yellow oil.

The synthetic route of 16744-81-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fuchida, Hirokazu; Tabata, Shigekazu; Shindo, Naoya; Takashima, Ippei; Leng, Qiao; Hatsuyama, Yuji; Hamachi, Itaru; Ojida, Akio; Bulletin of the Chemical Society of Japan; vol. 88; 6; (2015); p. 784 – 791;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem