Day: April 8, 2022

Electric Literature of 79055-63-3, 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. 79055-63-3, name is 2-Chloro-6-methylpyridin-4-amine. A new synthetic method of this compound is introduced below.

To a flask was added 2-chloro-4-(trifluoromethyl)-pyrimidine (1.50 g, 8.22 mmol), 2-chloro-6-methylpyridin-4-amine (1.17 g, 8.22 mmol), palladium acetate (0.18 g, 0.82 mmol), Xantphos (0.95 g, 1.64 mmol), and cesium carbonate (5.36 g, 16.44 mmol) followed by 1,4-dioxane (16.44 mL). The mixture was stirred at 100 C for 2 hours. The reaction was cooled to room temperature and was diluted with ethyl acetate and aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic fractions were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-50% ethyl acetate/hexanes) to afford N- (2-chloro-6-methylpyridin-4-yl)-4-(trifluoromethyl)pyrimidin-2-amine as a pale yellow solid. MS ESI calcd. for C11H9CIF3N4 [M + H]+ 289, found 289. XH NMR (500 MHz, DMSO-d6) delta 10.82 (s, 1H), 8.96 (d, J= 5.0 Hz, 1H), 7.78 (d, J= 1.5 Hz, 1H), 7.50 (d, J= 1.5 Hz, 1H), 7.48 (d, J= 5.0 Hz, 1H), 2.37 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,79055-63-3, 2-Chloro-6-methylpyridin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERCK CANADA INC.; ANTHONY, Neville, J.; ANDRESEN, Brian, M.; NORTHRUP, Alan, B.; CHILDERS, Kaleen, K.; DONOFRIO, Anthony; MILLER, Thomas, A.; LIU, Yuan; MACHACEK, Michelle, R.; WOO, Hyun Chong; SPENCER, Kerrie, B.; ELLIS, John Michael; ALTMAN, Michael, D.; ROMEO, Eric, T.; GUAY, Daniel; GRIMM, Jonathan; LEBRUN, Marie-Eve; ROBICHAUD, Joel, S.; WANG, Liping; DUBOIS, Byron; DENG, Qiaolin; WO2014/176210; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 709652-82-4, 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.709652-82-4, name is 2-Amino-5-bromonicotinonitrile, molecular formula is C6H4BrN3, molecular weight is 198.0201, as common compound, the synthetic route is as follows.

To a microwave reaction vessel were added 4-(tert- butoxycarbonylamino)phenylboronic acid (180 mg, 0.759 mmol), 5-bromo-3-cyano- 2-aminopyridine (170.0 mg, 0.858 mmol), 1,4-dioxane (3.5 mL) and 2M aqueous sodium carbonate (0.94 mL, 1.88 mmol). Argon gas was bubbled through the solution for 5 min, then tetrakis(triphenylphosphine) palladium(O) (40.0 mg, 0.035 mmol) was added and the vial was sealed and heated in a microwave reactor for 20 min at 170 C. The mixture was partitioned between EtOAc (10 mL) and saturated sodium bicarbonate (10 mL) The aqueous layer was separated and extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (10 mL), dried over MgS04, filtered and concentrated under reduced pressure to give an oil which was purified by silica gel flash chromatography, eluting with 25-100% EtOAc in hexanes. The purified material was dissolved in DCM (4 mL), excess TFA (2 mL) added and the mixture was stirred at rt for 4 h. The mixture was concentrated to dryness, then EtOAc (8 mL), saturated NaHC03 (8 mL) and 1 M aqueous NaOH (1 mL) were added. After confirming basic pH, the layers were shaken and separated and the aqueous layer was extracted with EtOAc (2 x 5 mL). The combined extracts were dried over MgS04, filtered and concentrated under reduced pressure to give 2- amino-5-(4-aminophenyl)nicotinonitrile (113.9 mg, 71%) as a solid, which was sufficiently pure for the next step. LC-MS (ESI) m/z 2 (M +H)+.

Statistics shows that 709652-82-4 is playing an increasingly important role. we look forward to future research findings about 2-Amino-5-bromonicotinonitrile.

Reference:
Patent; AMBIT BIOSCIENCES CORPORATION; ABRAHAM, Sunny; HOLLADAY, Mark, W.; LIU, Gang; XU, Shimin; WO2011/22473; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 851386-40-8, Adding some certain compound to certain chemical reactions, such as: 851386-40-8, name is 4-Chloro-2,5-difluoropyridine,molecular formula is C5H2ClF2N, 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 851386-40-8.

4-chloro-2,5-difluoropyridine E2 (1 .00 equivalents), 4-cyano-phenylboronic acid (1 .20 equivalents), Pd2(dba)3 (0.02 equivalent), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos) (0.08 equivalents) and tribasic potassium phosphate (2.50 equivalents) are stirred under nitrogen atmosphere in a dioxane/water mixture (ratio of 10:1 ) at 1 10 C for 20 h. To the reaction mixture Celite and active carbon are added and stirred at 1 10C for 15 min. Subsequently the reaction mixture is hot filtered and the residue washed with dioxane. The reaction mixture is poured into 200 mL of a saturated sodium chloride solution and extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried over MgSC>4 and the solvent is evaporated under reduced pressure. The crude product obtained is purified by recrystallization in cyclohexane and the product obtained as solid. (0422) Instead of a boronic acid a corresponding boronic acid ester may be used.The synthesis of Z3 is carried out according to AAV1-1, wherein 4-chloro-2,5-difluoropyridine E2 reacts with 3-cyano-phenylboronic acid ester. eneral procedure for synthesis AAV2-1:

According to the analysis of related databases, 851386-40-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CYNORA GMBH; ESTEBAN, Alhama Arjona; (133 pag.)WO2018/189356; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 54903-86-5, 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. 54903-86-5, name is 3-Bromopyridine-2,6-diamine. A new synthetic method of this compound is introduced below.

Preparation of N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61): A solution of 3-bromo-2,6-diaminopyridine (60) (564 mg, 3 mmol), triethyl amine (0.54 ml) in DCM (6 ml)/THF (4 ml) was cooled down to -78 C. A solution of 2-fluorobenzoyl chloride (362 mul, 3.03 mmol) in 2 ml DCM was added dropwise within 10 min. The resulting reaction mixture was stirred at -78 C. for 1 h before slowly warm up to r.t. After stirred at r.t. for 3 h, the reaction quenched with aq NaHCO3 solution. 200 ml EA were added. Org. phase was washed with brine, dried over sodium sulfate, concentrated. The light yellow solid residue was triturated with DCM (ca. 15 ml), filtered and dried to give 530 mg N-(6-amino-5-bromo(2-pyridyl))(2-fluorophenyl)carboxamide (61) as white solid. (purity>95%, yield: 57%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54903-86-5, 3-Bromopyridine-2,6-diamine, and friends who are interested can also refer to it.

Reference:
Patent; CalciMedica, Inc.; US2011/263612; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866775-18-0, 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 866775-18-0, name is Methyl 3-amino-6-bromo-5-(trifluoromethyl)picolinate. This compound has unique chemical properties. The synthetic route is as follows.

Intermediate A: 3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid3-Amino-6-bromo-5-trifluoromethyl-pyridine-2-carboxylic acid methyl ester (1.40 g, 4.68 mmol) was suspended in MeOH (15 ml); Sodium hydroxide (2.0 M aqueous solution) (14.04 ml, 28.1 mmol) was added and the suspension was stirred at RT overnight. The mixture was concentrated in vacuo and the resulting residue was dissolved in water (100 ml) and then acidifed by the addition of 5.0M HCl(aq). The product was extracted into ethyl acetate (2×75 ml) and the combined organic extracts were washed with water (50 ml), brine (25 ml), dried (MgSO4) and concentrated in vacuo to afford the title product as a yellow solid. 1H-NMR: [400 MHz, DMSO-d6, deltaH 13.24 (1H, br s, CO2H), 7.74 (1H, s, ArH), 7.17 92H, br s ArNH2). m/z 285.1, 287.1 [M+H]+

According to the analysis of related databases, 866775-18-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; US2011/230483; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 53636-68-3, 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. 53636-68-3, name is 3-Amino-5-chloropicolinic acid. A new synthetic method of this compound is introduced below.

3-Amino-5-chloropyridine-2-carboxylic acid (Int 2, 2 g, 11.6 mmol) was dissolved in NMP (100 mL) together with 1-amino-2-methyl-propan-2-ol (CAS: 2854-16-2, 1.14 g, 12.8 mmol), triethylamine (3.56 mL, 25.6 mmol) and HATU (4.87 g, 12.8 mmol). The resulting mixture was stirred at room temperature overnight. Next, the mixture was diluted with water and extracted with EtOAc. The organic fractions were combined, concentrated and the resulting crude residue was purified by column chromatography (petroleum ether/EtOAc 95/5 to 50/50) to give 3-amino-5-chloro-pyridine-2-carboxylic acid (2-hydroxy-2-methyl-propyl)-amide.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53636-68-3, its application will become more common.

Reference:
Patent; ABBVIE S.A.R.L.; GALAPAGOS NV; ALTENBACH, Robert, J.; COWART, Marlon, D.; DE MUNCK, Tom, Roger Lisette; DROPSIT MONTOVERT, Sebastien Jean, Jacques Cedric; GFESSER, Gregory, A.; KELGTERMANS, Hans; MARTINA, Sebastien, Laurent Xavier; VAN DER PLAS, Steven, Emiel; WANG, Xueqing; (300 pag.)WO2016/193812; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1033202-51-5, 5-Fluoro-3-nitropicolinonitrile, 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, 1033202-51-5, blongs to pyridine-derivatives compound. Application In Synthesis of 5-Fluoro-3-nitropicolinonitrile

Tin dichloride (45 g, 230 mmol) was added to a solution of 5-fluoro-3-nitropyridine-2-carbonitrile (Ark Pharm, 7.2 g, 43 mmol) in EtOH (80 mL). The mixture was stirred at 90 C. for 2 h, and then concentrated under reduced pressure. Aq. HCl (10 M; 40 mL, 400 mmol) was then added and the mixture was heated under reflux for 6 h. The reaction mixture was then concentrated under reduced pressure and the resulting residue was dissolved in MeOH (120 mL). Thionyl chloride (7.2 mL, 99 mmol) was added. The solution was then stirred at 90 C. for 24 h. The reaction mixture was concentrated under reduced pressure, diluted with EtOAc (300 mL), washed with a saturated aq. NaHCO3 (300 mL) and brine (200 mL), dried over Na2SO4 and concentrated again under reduced pressure. The resulting residue was purified by chromatography on silica gel (0-100% EtOAc in hexanes) to afford the sub-title compound (4.6 g, 63%). LCMS calc. for C7H8FN2O2 (M+H)+: m/z=171.0. found 171.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1033202-51-5, its application will become more common.

Reference:
Patent; INCYTE CORPORATION; Xue, Chu-Biao; Li, Yun-Long; Geng, Hao; Pan, Jun; Wang, Anlai; Zhang, Ke; Yao, Wenqing; Zhang, Fenglei; Zhuo, Jincong; US2014/200227; (2014); A1;,
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. 69045-78-9, name is 2-Chloro-5-(trichloromethyl)pyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 69045-78-9

Example 3 In a 119.5 cc autoclave equipped with a magnetic stirrer, 2-chloro-5-trichloromethylpyridine (11.5 g), Raney nickel (1.15 g), ethylenediamine (21.0 g) and ethanol (20 g) were charged. Hydrogen gas was introduced into the autoclave to a pressure of 10 Kg/cm2, and an internal temperature was raised to 45 C. At the same temperature, the hydrogen gas was supplied under a hydrogen pressure of 7 to 11.2 Kg/cm2. The absorption of hydrogen ceased after 180 minutes from the start of hydrogen supply. After completion of reaction, the autoclave was cooled down to room temperature, and the catalyst was filtrated off from the reaction mixture. The filtrate was adjusted to pH 13.7 with a 48% aqueous solution of sodium hydroxide and the filtrate was concentrated. The concentrate was analyzed by gas chromatography to find that a yield of 2-chloro-5-(2-aminoethyl)aminomethylpyridine was 10%.

The synthetic route of 69045-78-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Koei Chemical Co., Ltd.; US5424437; (1995); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1026796-81-5, N-(4-Bromopyridin-2-yl)acetamide, 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, 1026796-81-5, blongs to pyridine-derivatives compound. Application In Synthesis of N-(4-Bromopyridin-2-yl)acetamide

To the stirred solution of 3 -methyl- l-(6-(trimethy lstannyl)naphthalen-2- yl)butan-l-ol (0.080 g, 0.212 mmol) and (4-bromopyridin-2-yl)acetamide (0.046 g, 0.212 mmol) in anhydrous DMF (2 mL) was added tetrabutylammonium bromide (0.103 g, 0.318 mmol), bis(triphenylphosphine)palladium (II) chloride (0.019 g, 0.021 mmol), K2C03 (0.088 g, 0.636 mmol) and the mixture purged with nitrogen for 5 min then heated at 95 C for 14 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over Na2S04 and evaporated under reduced pressure. The residue was purified by preparative HPLC (0.1 % TF A in water and acetonitrile) to afford N-(4-(2-( 1 -hydroxy-3 – methylbutyl)quinolin-6-yl)pyridin-2-yl)acetamide, TFA (9 mg, 0.026 mmol, 12% yield). 1H NMR (400 MHz, CD3OD) delta ppm 8.98 (d, J= 8.8 Hz, 1H) 8.65 (d, J= 1.6 Hz, 1H) 8.40 – 8.49 (m, 3H) 8.30 (s, 1H) 8.04 (d, J= 8.8 Hz, 1H) 7.77 – 7.79 (m, 1H) 5.21 – 5.24 (m, 1H) 2.31 (s, 3H) 2.01 – 2.04 (m, 1H) 1.80 – 1.87(m, 1H) 1.69 – 1.75 (m, 1H) 1.00 – 1.12 (m, 6H); LCMS (ESI) m/e 350.2 [(M+H)+, calcd for C21H2 N3O2, 350.2]; LC/MS retention time (method A): tR = 1.62 min; HPLC retention time (method A): tR = 11.25 min.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1026796-81-5, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; WO2015/116492; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 884494-51-3, 2-Fluoro-4-iodonicotinic acid, 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: C6H3FINO2, blongs to pyridine-derivatives compound. COA of Formula: C6H3FINO2

Step 1: Methyl 2-(((3R,6R)-1-(tert-butoxycarbonyl)-6-methylpiperidin-3-yl)oxy)-4-iodonicotinate (15) A solution of 2-fluoro-4-iodonicotinic acid (0.651 g, 2.44 mmol) in DMF (3 mL) was treated with sodium hydride (0.072 g, 3.0 mmol). After stirring ~5 minutes, tert-butyl (2R,5R)-5- hydroxy-2-methylpiperidine-1-carboxylate (Example 2, 8, 0.500 g, 2.32 mmol) and sodium hydride 10 (0.072 g, 3.0 mmol) were added, and the reaction was heated to 40 C for 1 hour. Iodomethane (0.73 mL, 0.012 mmol) was added, and the reaction was stirred at RT. After 1 hour, the mixture was diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography eluting with 0-20% ethyl acetate in hexanes to provide the title compound as a colorless oil. LRMS m/z (M+H) 477.2 found, 477.2 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884494-51-3, 2-Fluoro-4-iodonicotinic acid, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/88864; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem