Tag: M.W:200-300

Electric Literature of 72587-15-6 , The common heterocyclic compound, 72587-15-6, name is 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine, molecular formula is C6H2ClF3N2O2, 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.

Step A. Alternative preparation of N-cyclobutyl-3-nitro-5-(trifluoromethyl)pyridin-2-amine To a mixture of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (1.00 g, 4.41 mmol) and NaHCO3 (1.12 g, 13.2 mmol) in EtOH (10 mL) was added cyclobutylamine (0.94 g, 13.2 mmol) drop-wise over 10 minutes. The mixture was stirred for 30 min, absorbed onto silica and purified on a 40 g ISCO gold silica gel column, eluting with a hexanes (100%) to hexanes (95%)/EtOAc (5%) gradient, to provide the desired compound (1.05 g, 91%) as a bright yellow solid.

The synthetic route of 72587-15-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KNOPP BIOSCIENCES LLC; Resnick, Lynn; Topalov, George T.; Boyd, Steven A.; Belardi, Justin K.; Flentge, Charles A.; Hale, James S.; Harried, Scott S.; Mareska, David A.; Zhang, Kai; Heap, Charles R.; Hadden, Mark; Cui, Wenge; Decornez, Helene; Liu, Shuang; (146 pag.)US2016/31875; (2016); 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. 603305-89-1, name is 7-Bromothieno[3,2-b]pyridine. A new synthetic method of this compound is introduced below., COA of Formula: C7H4BrNS

General procedure: Compound N13z (24.45 mg, 0.118 mmol) in 1,4-dioxane (2 ml) was added Pd2(dba)3 (10.76 mg, 0.012 mmol), XantPhos (13.6 mg, 0.0235 mmol), 4-bromoquinoline (50 mg, 0.118 mmol), and DIPEA (61.4 muL, 0.353 mmol). The reaction vessel was degassed with argon, sealed, and heated to 110 C. overnight. The reaction mixture was then cooled to room temperature, filtered through Celite, and concentrated. The resulting residue was concentrated, diluted with 1:1 acetonitrile and water each containing 0.1% TFA and purified on preparatory HPLC (0 to 100% acetonitrile in water each containing 0.1% TFA). This provided Compound E78a as a TFA salt. LCMS ESI+ calc’d for C29H34N6O2S: 531.3 [M+H+]. found: 531.2 [M+H+].

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, 603305-89-1, 7-Bromothieno[3,2-b]pyridine.

Reference:
Patent; Gilead Sciences, Inc.; Chin, Gregory; Clarke, Michael O’ Neil Hanrahan; Han, Xiaochun; Hansen, Tim; Hu, Yunfeng Eric; Koltun, Dmitry; McFadden, Ryan; Mish, Michael R.; Parkhill, Eric Q.; Sperandio, David; Xu, Lianhong; Yang, Hai; (199 pag.)US2020/108071; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 955369-63-8, 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.955369-63-8, name is Ethyl 2-(6-bromopyridin-2-yl)acetate, molecular formula is C9H10BrNO2, molecular weight is 244.09, as common compound, the synthetic route is as follows.

To a mixture of ethyl 2-(6-bromo-2-pyridyl)acetate (2.00 g, 8.19 mmol) in THF (10 mL), water (10 mL) and MeOH (20 mL) was added LiOH.H2O (1.03 g, 24.5 mmol). Then the reaction mixture was stirred at 20 C for 2 hours. On completion, the reaction mixture was concentrated in vacuo. The residue was acidified by 1.0 N HCl to pH = 3.0, washed with water (150 mL) and extracted with ethyl acetate (3 X 150 mL). The organic layer was dried with Na2SO4, filtered and concentrated in vacuo to give the title compound (1.70 g, 96% yield) as a yellowish solid.1H NMR (400MHz, DMSO-d6) delta = 12.63 (br. s., 1H), 7.86 – 7.71 (m, 1H), 7.59 (d, J = 8.0 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 3.81 (s, 2H).

Statistics shows that 955369-63-8 is playing an increasingly important role. we look forward to future research findings about Ethyl 2-(6-bromopyridin-2-yl)acetate.

Reference:
Patent; RAZE THERAPEUTICS, INC.; MAINOLFI, Nello; (215 pag.)WO2018/106636; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 105752-11-2, 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.105752-11-2, name is 3-Amino-4-iodopyridine, molecular formula is C5H5IN2, molecular weight is 220.0111, as common compound, the synthetic route is as follows.

2,6-dichloro-[3,4′-bipyridin]-3′-amine (i64): To a stirred solution of 4-iodopyridin-3-amine (2 g, 9.0 mmol) in 1 ,4-dioxane (84 ml_), (2,6- dichloropyridin-3-yl) boronic acid (2.4 g, 12.5 mmol) and K3P04 (5.6 g, 26.0 mmol) solution in water (28 mL) were added and the reaction was degassed with argon for 20 min. PdCI2(PPh3)2 (0.7 g, 0.99 mmol) was added and the reaction was heated in a sealed tube at 100C for 16 h. The progress of the reaction was monitored by TLC. After completion, the reaction was diluted with water and filtered. The aqueous layer was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by silica gel (100:200 mesh) column chromatography using 2% methanol in dichloromethane as eluent to afford 2,6-dichloro-[3,4′-bipyridin]-3′-amine (64) (1 .08 g, Yield 51 %). 1 H NMR (400 MHz, DMSO-d6) delta 5.26 (s, 2H), 6.93 (d, J = 4.9 Hz, 1 H), 7.51 -7.68 (m, 1 H), 7.79- 7.89 (m, 2H), 8.08 (s, 1 H), MS (ESI) m/e (M+1 )+: 240.00

Statistics shows that 105752-11-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-4-iodopyridine.

Reference:
Patent; UCB BIOPHARMA SPRL; MERCIER, Joel; PROVINS, Laurent; VERMEIREN, Celine; SABNIS, Yogesh Anil; (106 pag.)WO2016/124508; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 70201-42-2, 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.70201-42-2, name is 3,5-Dibromoisonicotinaldehyde, molecular formula is C6H3Br2NO, molecular weight is 264.9, as common compound, the synthetic route is as follows.

To a solution of cesium carbonate (9.20 g, 28.2 mmol) and 4-phenylphenol (2.40 g, 14.1 mmol) in anhydrous THF (100 mL) under an inert atmosphere was added a solution of 3,5-dibromopyridine-4-carboxaldehyde (7.48 g, 28.2 mmol) in THF (25 mL). The reaction mixture was heated at reflux for 4 hours then was allowed to cool to room temperature. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was diluted with EtOAc, washed with aqueous sodium bicarbonate, washed with brine, and dried over sodium sulfate then filtered and the solvent removed in vacuo. Purification by silica gel (eluting with 20% EtOAc: heptane) followed by recrystallization from heptane afforded 3- (bipfienyl-4-yloxy )-5-bronio-pyridine-4-carbaldehyde (4.39 g, 12.4 mmol, 87%); (at)H-NMR (DMSO-d6, 400 MHz) : 8 7.23 (m, 2H), 7.38 (m, 1H), 7.47 (m, 2H), 7.66 (m, 2H), 7.73 (m, 2H), 8.43 (s, 1H). RP-HPLC (Table 1, Method i) R(at) = 3.72 min.

Statistics shows that 70201-42-2 is playing an increasingly important role. we look forward to future research findings about 3,5-Dibromoisonicotinaldehyde.

Reference:
Patent; ABBOTT LABORATORIES; WO2005/110410; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1659-31-0, 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. 1659-31-0, name is Dipyridin-2-yl carbonate. A new synthetic method of this compound is introduced below.

Under nitrogen atmosphere, to a stirred mixture of (4-cyclohexylphenyl)-methanol (0.3 g, 1.58 mmol) in dry CH2C12 (2 mL), DMAP (0.019 g, 0.16 mmol) and di-2-pyridyl- carbonate (0.41 1 g, 1.90 mmol) were added. The reaction mixture was left to react at rt for 15 h, then diluted with CH2C12 and washed first with a saturated NH4C1 solution (3.0 mL) and subsequently with a saturated NaHC03 solution (3X3 mL). The organic fraction was dried over Na2S04, filtered and concentrated to dryness to afford a colorless oil (0.464 g, 95%), as a mixture (ratio 1.8: 1) of (4-cyclohexylphenyl)-methyl-2-pyridyl carbonate and (4- cyclohexylphenyl)-methy 1-2 -oxopyridine-1 -carboxylate. The mixture of isomers was not separated and used in the next step without any further purification. MS (ESI) m/z 350 [M- K]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1659-31-0, Dipyridin-2-yl carbonate, and friends who are interested can also refer to it.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; IIT – ISTITUTO ITALIANO DI TECNOLOGIA; UNIVERSITY DEGLI STUDI DI URBINO; UNIVERSITA DEGLI STUDI DI PARMA; PIOMELLI, Daniele; BANDIERA, Tiziano; MOR, Marco; TARZIA, Giorgio; BERTOZZI, Fabio; PONZANO, Stefano; WO2013/78430; (2013); A1;,
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. 116026-93-8, name is tert-Butyl (3-formylpyridin-4-yl)carbamate, molecular formula is C11H14N2O3, 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. Quality Control of tert-Butyl (3-formylpyridin-4-yl)carbamate

Preparation 56 : 2-tert-Butoxycarbonylamino-3-(4-tert-butoxycarbonylaminopyridin-3-yl) acrylic acid methyl ester; To a solution of (+/-)-Boc-alpha-phosphonoglycine trimethyl ester (1.5Og, 5.05mmol) in dry THF (2OmL) at -780C was added 1,1,3,3-tetramethylguanidine (0.6OmL, 4.78mmol) and the mixture was stirred in the cold for 20min. A solution of 4-[N-(tert-butyloxycarbonyl)amino]-3- pyridinecarboxaldehyde (Preparation 55, 1.Og, 4.50mmol) in dry THF (1OmL) was added slowly and the resulting mixture allowed to warm up to rt and stirred for additional 12h before being poured into water (20OmL). Extraction with EtOAc (3x75mL) and washing of the combined extracts with brine (5OmL) gave after drying (MgSO4) and concentration in vacuo an oily residue. Purification of the residue by flash chromatography on silica gel (eluent: toluene / acetone : 2 /1) gave the title compound as colourless oil. delta? (CDCl3): 1.31 (9H, s), 1.53 (9H, s), 3.91 (3H, s), 6.61, 6.76 (2H, 2 xbr s), 7.05 (IH, s), 8.06 (IH, d), 8.37-8.39 (2H, m); m/z (ES+) = 394.13 [M+H]+; RT = 2.81 min.

With the rapid development of chemical substances, we look forward to future research findings about 116026-93-8.

Reference:
Patent; PROSIDION LIMITED; WO2006/59164; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 944317-53-7, 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. 944317-53-7, name is 4-Methyl-5-nitro-2-(trifluoromethyl)pyridine, molecular formula is C7H5F3N2O2, 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.

A solution of 6.0 g (23.29 mM) of 4-methyl-5-nitro-2-trifluoromethylpyridine (Preparation 4) in 14.8 mL (109.45 mM) diethyl oxalate was prepared. 8.65 g (56.8 mM) of DBU were added and the mixture was stirred for 4 hours at room temperature. The medium was concentrated under reduced pressure and the residue was then dissolved in 120 mL of acetic acid. This mixture was brought to 60 C. and 2.60 g (46.6 mM) of iron were added. The medium was heated at 70 C. overnight. The medium was diluted with water and the precipitate formed was filtered off and washed three times with water. The solid was dissolved in ethyl acetate, and the solution was filtered. The filtrate obtained was concentrated under reduced pressure. The title product was obtained in the form of a brown solid (5.70 g, yield=95%). m.p.=142 C

According to the analysis of related databases, 944317-53-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Laboratoires Fournier SA; US2012/302560; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 884495-14-1 ,Some common heterocyclic compound, 884495-14-1, molecular formula is C7H7BrN2O3, 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.

DMF-DMA (600 mL) was slowly added to a stirred and heated (80 C) solution of 5-bromo-2- methoxy-4-methyl-3-nitropyridine (134 g, 0.54 mol) in DMF (1.1 L). After addition, the mixture was heated at 95 C for 5 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled to room temperature and poured into ice-cold water (3 L). The resulting red solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (167 g, 100% yield) as red solid. 1H NMR (400 MHz, DMSO-tM): delta 8.24 (s, 1 H), 7.05 (d, J= 13.6 Hz, 1 H), 7.05 (d, J= 13.6 Hz, 1 H), 4.80 (d, J= 13.2 Hz, 1 H), 3.88 (s, 3 H), 2.90 (s, 6 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-14-1, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HSIAO-WEI TSUI, Vickie; HEWITT, Michael, Charles; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F., Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (251 pag.)WO2016/77375; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 58530-53-3, 2,4-Dibromopyridine, 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 2,4-Dibromopyridine, blongs to pyridine-derivatives compound. Application In Synthesis of 2,4-Dibromopyridine

Preparation of 4-bromo-2-phenylpyridine Into a 500 mL round-bottomed flask was placed 2,4-dibromopyridine (9.90 g, 41.8 mmol), phenylboronic acid (5.10 g, 41.8 mmol), and potassium carbonate (11.55 g, 84 mmol) in DME (100 mL). The reaction mixture was diluted with water (40 mL). This was degassed for 30 minutes and Pd(PPh3)4, (0.483 grams, 0.418 mmol) was added and the reaction was stiffed at reflux for 22 hours. The mixture was diluted with brine and ethyl acetate. The organic layer was washed with water, dried and adsorbed onto Celite and chromatographed on a 400 gram column eluted with 0-5% ethyl acetate in hexane giving the desired product (5.30 g, 54%) as clear colorless oil.

The synthetic route of 58530-53-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universal Display Corporation; Beers, Scott; Xia, Chuanjun; Layek, Suman; Wendt, Harvey; US2014/8617; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem