Month: April 2022

Application of 19235-89-3, 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. 19235-89-3, name is 4-Chloropyridine-2-carbonitrile, molecular formula is C6H3ClN2, 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 A15 A teflon capped vial was charged with 4-amino-3-fluorophenol (0.291 g, 2.29 mmol) and anhydrous DMF (2.3 mL). The resultant solution was de-gassed in vacuo and backfilled with argon (3*). The vial was treated with sodium tert-butoxide (0.27 g, 2.41 mmol) under argon and quickly capped. The reaction mixture was stirred at RT for 1 h. After addition of 4-chloropicolinonitrile (0.317 g, 2.29 mmol) and K2CO3 (0.174 g, 1.26 mmol), the vial was de-gassed again and heated in a 90 C. oil bath overnight. The reaction mixture was diluted with EtOAc (60 mL) and washed with brine (25 mL). The aqueous phase was back-extracted with EtOAc (50 mL). The combined organic layers were washed with brine (25 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography to afford 4-(4-amino-3-fluorophenoxy)picolinonitrile (0.162 g, 31% yield) as a colorless oil. 1H NMR (DMSO-d6) delta 8.56 (d, J=5.6 Hz, 1H), 7.62 (d, J=2.0 Hz, 1H), 7.14 (dd, J=6.0, 2.8 Hz, 1H), 7.03 (dd, J=11.6, 2.4 Hz, 1H), 6.88-6.77 (m, 2H), 5.25 (s, 2H); MS (ESI) m/z: 230.0 (M+H+).

According to the analysis of related databases, 19235-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; US2008/90856; (2008); 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. 39856-57-0, name is 2,6-Dibromopyridin-3-amine, molecular formula is C5H4Br2N2, 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. COA of Formula: C5H4Br2N2

Sodium methoxide (176.2 g, 3.26 mol) was added in portions to a sol. of 3-amino-2,6- dibromopyridine (100 g, 939 mmol) in 1,4-dioxane (1 1) and the r.m. was stirred under reflux for 3 h. After cooling, the r.m. was poured onto a sat. aq. NH4C1 aq. sol (1 1). Additional NH4CI (150 g) and H20 (1 1) were added and the r.m. was stirred at r.t. for 30 min. Et20 (2 1) was added and the r.m. was stirred for 30 min. The layers were separated and the aq. layer was diluted with H20 (1.5 1) and further extracted with Et20 (6 x 0.5 1). The combined o.l. were treated with brine (2 x 0.5 1), dried (MgS04) and cone, under reduced pressure to give a black residue. The residue was purified by flash chromatography over silicagel (glas filter, eluent DCM). The product fractions were combined and cone, under reduced pressure to afford an orange-brownish solid residue. Yield: 67.2 g of intermediate 24 (78.3 %).

With the rapid development of chemical substances, we look forward to future research findings about 39856-57-0.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; DE CLEYN, Michel, Anna, Jozef; VAN BRANDT, Sven, Franciscus, Anna; GIJSEN, Henricus, Jacobus, Maria; BERTHELOT, Didier, Jean-Claude; OEHLRICH, Daniel; WO2011/86098; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 348640-02-8, 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 348640-02-8 as follows.

A solution of 209-2 (50.0 g, 183.8 mmol) in dry THF cooled to -78 C. and n-BuLi (81 ml, 2.5 M in hexane) was added over 20 minutes. The resulted solution was maintained at -78 C. for 1 h, and then a solution of BrCl2CCCl2Br (71.0 g, 220.5 mmol) in dry THF was added. The mixture was stirred -78 C. for 30 min and allowed to warm slowly to room temperature. The solvent was removed under vacuum and the residue was partitioned between EtOAc and water. The organic layer was dried over anhydrous Na2SO4 and concentrated. The crude product was purified by column chromatography (5% ethyl acetate in petroleum ether to 20% ethyl acetate in petroleum ether as the eluent) to afford 209-3 (37 g, 58% yield). MS-ESI: m/z=351.0 [M+1]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,348640-02-8, its application will become more common.

Reference:
Patent; INTERMUNE, INC.; US2009/318455; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 107351-82-6, name is 2-Bromo-5-phenylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 107351-82-6

General procedure: Intermediate M1 (43.6 g, 0.1 mol), iodobenzene (24.5 g, 0.12 mol), CuI (3.3 g, 17.1 mmol), K3PO4 (21.8 g, 102.9 mmol), ethylenediamine (2.3 ml, 34.3 mmol) and toluene (500 ml) were mixed.After stirring for 1 day under reflux, after the reaction was completed, it was cooled to room temperature, and the organic layer was extracted with ethyl acetate (EA) and distilled under reduced pressure. the obtained distillation residue was subjected to column separation (eluent: EA/hexane), compound A1 (35.7 g, 70.1%) was obtained.

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, 107351-82-6, 2-Bromo-5-phenylpyridine.

Reference:
Patent; Wuhan Shengchengyu Technology Co., Ltd.; Huang Yupeng; Qin Wei; Gao Dewen; Tan Yao; (19 pag.)CN109096281; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16727-47-2, 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. 16727-47-2, name is 2,6-Bis(benzyloxy)-3-bromopyridine. A new synthetic method of this compound is introduced below.

A stirred mixture of 16-1 (170 mg, 459 mumol), 23-1 (124.8 mg 918 mumol) and Potassium phosphate (211 mg, 918 mumol) in Dioxane:water (6:1, 7 mL) was degassed with argon for 10 minutes. PdCl2dppf.DCM (38 mg, 45.9 mumol) was added and stirred the reaction was stirred at 110C for 16 hours, cooled to room temperature and then filtered through a short bed of celite. The filtrate was diluted with Ethyl acetate, washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude mass was purified by column chromatography (silica, gradient: 0-5% Ethyl acetate in Hexane) to afford 23-2 (160 mg, 419 mumol, 91%) as a sticky solid. LC MS: ES+ 382.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,16727-47-2, 2,6-Bis(benzyloxy)-3-bromopyridine, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; HE, Minsheng; LAZARSKI, Kiel; VEITS, Gesine, Kerstin; VORA, Harit, U.; (794 pag.)WO2017/197046; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 98139-15-2, 4-Aminopicolinonitrile, 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, COA of Formula: C6H5N3, blongs to pyridine-derivatives compound. COA of Formula: C6H5N3

Ethyl 4-chlorosulfonyl-3-fluoro-l-methyl-pyrrole-2-carboxylate (1500 mg, 5.56 mmol) was dissolved in dry pyridine (26.25 mL, 325.2 mmol). l-(trifluoromethyl)cyclopropan-l -amine (1392 mg, 11.1 mmol) was added and the mixture was stirred at 70C for 6 hours. The mixture was concentrated in vacuo. The obtained residue was purified by silica gel column (0877) chromatography using gradient elution from heptane to EtOAc (100:0 to 0: 100) yielding ethyl 3-fluoro- 1 -methyl-4-[[ 1 -(trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (1.21 g) as a beige powder. Ethyl 3-fluoro-l-methyl-4-[[l- (0878) (trifluoromethyl)cyclopropyl]sulfamoyl]pyrrole-2-carboxylate (0.15 g, 0.31 mmol) and (0879) 4-aminopyridine-2-carbonitrile (40.05 mg, 0.34 mmol) were dissolved in THF (3 mL) in a tube. The tube was flushed with nitrogen, capped with a septum and stirred at room temperature. To this was added lithium bis(trimethylsilyl)amide (0.76 mL, 1 M, 0.76 mmol) at once using a syringe. The obtained solution was stirred for 3 hours. Then ammonium chloride (aq. / sat. / 10 mL) was added and the layers where separated. Then it was extracted once using ethyl acetate (10 mL). The combined extracts were concentrated in vacuo and purified by silica gel column chromatography using gradient elution from heptane to EtOAc. (100:0 to 0:100). The obtained fractions were concentrated in vacuo and repurified by Prep HPLC on (RP SunFire Prep CI 8 OmicronBeta-10muetaiota,30chi150etaiotaetaiota). Mobile phase (0.25% NH4HCO3 solution in water, MeOH). The desired fractions were concentrated under reduced pressure and co-evaporated twice with methanol (2 X 20 mL) and dried in a vacuum oven at 55C for 18 hours resulting in compound 192 (51 mg) as a white powder. Method B: Rt: 0.90 min. m/z: 430.1 (M-H)” Exact mass: 431.1. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.14 – 1.30 (m, 4 H), 3.75 – 3.89 (m, 3 H), 7.57 (d, J=4.6 Hz, 1 H), 7.90 (dd, J=5.6, 2.1 Hz, 1 H), 8.21 (d, J=2.0 Hz, 1 H), 8.63 (d, J=5.7 Hz, 1 H), 9.15 (br. s., 1 H), 10.67 (br. s., 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,98139-15-2, 4-Aminopicolinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; JANSSEN SCIENCES IRELAND UC; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; LAST, Stefaan Julien; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2015/118057; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 185041-05-8, Methyl 2-chloro-4-iodonicotinate, 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, Computed Properties of C7H5ClINO2, blongs to pyridine-derivatives compound. Computed Properties of C7H5ClINO2

Amixture of methyl 2-chloro-4-iodonicotinate (1.00 g, 3.29 mmol, 98% puritycalculated by LC-MS analysis), (4-chlorophenyl)boronic acid (0.630 g, 4.03mmol), PdCl2(dppf) (0.246 g, 0.336 mmol) and K2CO3(1.39 g, 10.1 mmol) in dioxane (50 mL) and water (10 mL) was heated to 90 Cand stirred for 15 h. The reaction mixture was concentrated in vacuo and the residue was dilutedwith EtOAc (20 mL) and water (20 mL). The organic phase was separated and theaqueous phase was extracted with EtOAc (2 x 10 mL). The combined organic phasewas washed with brine (20 mL), dried with anhydrous Na2SO4,filtered and concentrated in vacuo. Theresidue was purified by flash column chromatography on silica gel (Petroleumether/EtOAc = 30/1 to 20/1) to afford methyl 2-chloro-4-(4-chlorophenyl)nicotinate (0.850 g, 82%) as a yellow solid. 1H NMR (400 MHz, CDCl3)delta 3.79 (3H, s), 7.28 (1H, s), 7.35-7.38 (2H, m), 7.43-7.47 (2H, m), 8.50 (1H,d, J = 5.2 Hz). MS (ESI) m/z: 282.0 [M+H]+.

The synthetic route of 185041-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Miyazaki, Tohru; Kawasaki, Masanori; Suzuki, Atsushi; Ito, Yuki; Imanishi, Akio; Maru, Takamitsu; Kawamoto, Tomohiro; Koike, Tatsuki; Bioorganic and Medicinal Chemistry Letters; vol. 29; 6; (2019); p. 815 – 820;,
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.1124-29-4, name is 5-Acetylpyridin-2(1H)-one, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Acetylpyridin-2(1H)-one

2- methoxy-5-acetyl pyridine (1.51 g, 10 mmol) was treated with 6N HCl at 100C for 5 hours. The reaction mixture was neutralized with sodium hydroxide to pH 7 and then extracted several times with DCM. Organic layer was dried over sodium sulfate, evaporated and the residue was crystallized from ethyl acetate to give 5-acetyl-2(lH)- pyridone as a white solid, 1.06 g (78%). This compound (685.7 mg, 5 mmol) was reacted with iodobenzene (0.84 ml, 7.5 mmol) in the presence of CuI (95 mg, 0.5 mmol) and K2CO3 (691 mg, 5 mmol) in DMF (5 ml) at 1350C overnight. The reaction mixture was diluted with 10% ammonia (15 ml) and extracted with ethyl acetate. The organic extract was washed with saturated sodium chloride, dried over magnesium sulfate and evaporated. Column chromatography (10% ethyl acetate-DCM) afforded 407 mg (38%) of the target compound as a white solid. The 1H NMR spectra was consistent with the structure of Compound 16.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1124-29-4, 5-Acetylpyridin-2(1H)-one, and friends who are interested can also refer to it.

Reference:
Patent; INTERMUNE, INC.; WO2006/122154; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 28900-10-9, 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. 28900-10-9, name is 2-Chloro-6-methylnicotinonitrile, molecular formula is C7H5ClN2, 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.

To a solution of 2-chloro-3-cyano-6-methylpyridine (6.10 g) was added a 28% aqueous ammonia solution (70 mL)The reaction was carried out in an autoclave at 170 C for 7 hours. The reaction solution was cooled to room temperature,The ammonia was removed under reduced pressure Add potassium hydroxide (9.00 g) to the reaction mixture by removal of ammonia, and heated at 100 C under stirring for 3 hours. The reaction mixture was cooled to room temperature, 4N hydrochloric acid was added dropwise and the pH was adjusted to 4-5. The precipitated crystals were collected by filtration, further washed with water and air dried them. To obtain 2-amino-6-methyl nicotinic acid 5.04g (yield 82.9%). With the implementation of purity liquid chromatography analysis showed a high purity of 97.06%.

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 28900-10-9, 2-Chloro-6-methylnicotinonitrile.

Reference:
Patent; AGRO-KANESHO CO.,LTD; AIZAWA, RYO; ARAKI, KOICHI; (13 pag.)TW2016/509; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 183208-34-6, 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 183208-34-6, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one. This compound has unique chemical properties. The synthetic route is as follows.

Synthesized according to Procedure J-1. 1H NMR 400 MHz (DMSO-d6) delta 11.02 (s, 1H); 8.07 (s, 1H); 7.88 (s, 1H); 7.71 (s, 1H); 4.40 (m, 2H); 1.34 (m, 3H).

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 183208-34-6, 5-Bromo-1H-pyrrolo[2,3-b]pyridin-2-one.

Reference:
Patent; Glaxo Wellcome Inc.; US6350747; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem