Pyridine-derivatives

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 131748-14-6, name is 4-Chloro-(2-trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C6H3ClF3N

To a solution of N-feri-butyloxycarbonyl-protected tyramine (130 g, 550 mmol), potassium carbonate (76 g, 550 mmol), and catalytic amounts of potassium iodide in N-methyl pyrrolidone (NMP, 400 ml.) that was stirred for 10 minutes at room temperature was added 4-chloro-2- trifluoromethylpyridine (100 g, 550 mmol). The reaction mixture was then heated to 160 C for 6 h, cooled, poured into water and extracted with methyl-feri-butylether (MTBE, 3x). The combined organic layers were washed with succesivly with 3 N NaOH and water, dried over Na2S04, and reduced in vacuo. The crude residue was purified by flash silica gel column chromatography to afford a 48% (102 g, 265 mmol) yield of N-tert-butyloxycarbonyl-protected 2-[4-[[2-(trifluoromethyl)-4-pyridyl]oxy]phenyl]ethanamine. To a solution of this material in dioxane (200 ml.) was added 4 M HCI in dioxane (250 ml_). The solution was left overnight to stir at room temperature, which resulted in precipitation of 2-[4-[[2-(trifluoromethyl)-4- pyridyl]oxy]phenyl]ethanamine hydrochloride. The reaction solution was evaporated and the residue was stirred with pentane and filtered to provide 100% (37 g, 104 mmol) of the desired amine hydrochloride.

With the rapid development of chemical substances, we look forward to future research findings about 131748-14-6.

Reference:
Patent; BASF SE; BASF SCHWEIZ AG; GRAMMENOS, Wassilios; CRAIG, Ian Robert; BOUDET, Nadege; MueLLER, Bernd; DIETZ, Jochen; LAUTERWASSER, Erica May Wilson; LOHMANN, Jan Klaas; MONTAG, Jurith; VRETTOU-SCHULTES, Marianna; WO2013/113778; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 122368-54-1, 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. 122368-54-1, name is 2-((4-Chlorophenyl)(piperidin-4-yloxy)methyl)pyridine. A new synthetic method of this compound is introduced below.

EXAMPLE 47 From 4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine and 5-chloro-2-pentanone, 5-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-2-pentanone was obtained in the same procedure as described in Example 26. Mass analysis value: EI-MS M+ no peak, CI-MS m/e=387(M+ +1). 1 H-NMR(CDCl3): delta(ppm)=1.60-1.95(6H,b,m), 2.08(2H,b), 2.14(3H,s), 2.27(2H,t), 2.43(2H,t), 2.70(2H,b), 3.44(1H,m), 5.59(1H,s), 7.11-7.71(7H,m), 8.50(1H,m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122368-54-1, its application will become more common.

Reference:
Patent; Ube Industries, Ltd.; US4929618; (1990); A;,
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. 6313-54-8, name is 2-Chloroisonicotinic acid, molecular formula is C6H4ClNO2, 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. Recommanded Product: 2-Chloroisonicotinic acid

2-Chloro-N-(4-phenylpyridin-3-yl)isonicotinamide (alternative synthesis). To 4- phenylpyridin-3 -amine (0.5 g, 2.94 mmol) and 2-chloroisonicotinic acid (0.486 g, 3.08 mmol) in EtOAc (10 mL) was added DIEA (2.57 mL, 14.69 mmol) followed by T3P, 50% in EtOAc (2 mL, 3.43 mmol). The reaction was stirred at rt overnight. It was diluted with EtOAc and washed with water, brine and dried over sodium sulfate. The crude product was dissolved in a small amount of dichloromethane and charged to a 120 g silica gel cartridge which was eluted with 0-15% dichloromethane / methanol over a period of 40 mins. The desired fractions were combined and dried under vacuo to give 2-chloro-N-(4-phenylpyridin-3-yl)isonicotinamide (0.75g, 2.421 mmol, 82 % yield). MS (ESI) (m/z): 310.0(M+H)+.

With the rapid development of chemical substances, we look forward to future research findings about 6313-54-8.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1480-87-1, 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 1480-87-1, name is 2-Fluoro-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Example 32; Protocol for the preparation of terf-butyl 3-(3-(2-(methoxycarbonyl)-3- methylbenzo[b]thiophen-4-ylamino)pyridin-2-yloxy)azetidine-1-carboxylate; a) Preparation of terf-butyl 3-(3-nitropyridin-2-yloxy)azetidine-1-carboxylate; Sodium hydride (60 % dispersion in oil, 2.30 g, 57.64 mmol) was added portionwise into a solution of 1 -Boc-3-(hydroxy)azetidine (9.94 g, 57.64 mmol) in anhydrous THF (110 mL) at 0 C and stirred for 0.5 hour. A solution of 2-fluoro-3-nitro-pyhdine (7.80 g, 54.9 mmol) in anhydrous THF (15 mL) was added drop wise and the mixture allowed to warm to ambient temperature overnight. The mixture was cooled in an ice- bath and water (50 mL) added. The product was extracted with EtOAc, washed with water, brine and dried (Na2SO4). The product was purified by flash- column chromatography (petroleum ether (40-60 0C)/ DCM) to yield the title compound as a yellow solid (4.37 g, 27 %).1H NMR (400 MHz; CDCI3; 25 C): delta 8.36 (m, 1 H), 8.30 (d, 1 H), 7.09 (m, 1 H), 5.45 (m, 1 H), 4.35 (m, 2H), 4.06 (m, 2H), 1.45 (s, 9H). MS (ESI+): 296 (M+H). HPLC (10cm_esci_BICARB): Rt 3.47 min (HPLC purity 93 %).

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 1480-87-1, 2-Fluoro-3-nitropyridine.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; AUSTEN, Matthias; BLACK, Phillip; BLACKABY, Wesley; DANILEWICZ, John; LINNEY, Ian; SCHREITER, Kay; SCHNEIDER, Martin; WO2010/23181; (2010); 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. 58530-50-0, name is 2-(Pyridin-2-yloxy)acetic acid, molecular formula is C7H7NO3, 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. Recommanded Product: 58530-50-0

5-(4-Aminophenyl)-1H-naphtho[1,2-e][1,4]diazepin-2(3H)-one (82 mg, 0.531 mmol) obtained in Example 1, (1), 2-(pyridyl-2-yloxy)acetic acid (47 mg, 0.314 mmol), HATU (302 mg, 0.795 mmol), diisopropylethylamine (138 mg, 1.06 mmol), and dimethylformamide (10 mL) were mixed, and the mixture was stirred at room temperature for 16 hours under a nitrogen atmosphere. To the reaction mixture, saturated aqueous sodium hydrogencarbonate was added, and the resulting mixture was extracted with ethyl acetate. Purification was performed in a conventional manner to obtain the title compound (25 mg, yield 21%) as white solid. 1 H NMR (DMSO-d6, 400 MHz) delta: 3.76 (1H, d, J=10Hz), 4.55 (1H, d, J=10Hz), 4.95 (2H, s), 6.9-7.0 (2H, m), 7.29 (1H, d, J=9Hz), 7.51 (2H, d, J=8Hz), 7.6-7.7 (6H, m), 8.01 (1H, br s), 8.14 (1H, d, J=4Hz), 8.39 (1H, br s), 10.34 (1H, br s), 10.83 (1H, br s)

With the rapid development of chemical substances, we look forward to future research findings about 58530-50-0.

Reference:
Patent; Nippon Chemiphar Co., Ltd.; Kyushu University; SAKUMA, Shogo; KOBAYASHI, Kunio; USHIODA, Masatoshi; IMAI, Toshiyasu; INOUE, Kazuhide; (36 pag.)EP3020707; (2016); A1;,
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.847375-33-1, name is Ethyl 2-(5-bromopyridin-3-yl)acetate, molecular formula is C9H10BrNO2, molecular weight is 244.0852, as common compound, the synthetic route is as follows.Recommanded Product: 847375-33-1

Step 9: 3-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid benzyl ester (1.96 g, 3.7 mmol), (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (0.99 g, 4.1 mmol), and potassium carbonate (1.79 g, 13.0 mmol) were combined in DME (40 mL) and H2O (30 mL), and the solution was purged with N2 for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.427 g, 0.37 mmol) was added, and the reaction was stirred at 70 C. overnight. The mixture was quenched with 1N aqueous HCl(13 mL) and extracted with EtOAc. The combined organic layers were washed with H2O, and then dried and concentrated to give 3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid benzyl ester.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,847375-33-1, Ethyl 2-(5-bromopyridin-3-yl)acetate, and friends who are interested can also refer to it.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; US2010/81673; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 153034-82-3, 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. 153034-82-3, name is 2-Fluoro-4-iodonicotinaldehyde. A new synthetic method of this compound is introduced below.

a) Hydrazine monohydrate (0.78 mL, 15.94 mmol) was added dropwise to a suspension of 2-fluoro-4-iodonicotinaldehyde (2.00 g, 7.97 mmol) in 2-propanol (20 mL) and heated at 60 C. After 2 h, the solvent was removed by rotatory evaporation and the residue dissolved in EtAcO (40 mL) and washed with water (30 mL). The organic layer was dried over anhydrous Na2S04 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (10D40% EtAcO/hexanes), affording 1 .62 g of 4-iodo-1 H-pyrazolo[3,4-b]pyridine, [Rf= 0.30 (20% EtAcO/hexanes), white solid, 82% yield].LC-MS ESI+ m/z: 246 (M+1 , 99%) (Method 5).1 H-NMR (CDCI3, 250 MHz, ?) : 12.45 (br s, 1 H); 8.23 (d, J= 5.0 Hz, 1 H, ArH); 7.98 (s, 1 H, ArH); 7.61 (d, J= 5.0 Hz, 1 H, ArH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,153034-82-3, 2-Fluoro-4-iodonicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; LABORATORIOS DEL DR. ESTEVE, S.A.; DRACONIS PHARMA, S.L.; ALMIRALL, S.A.; TORRENS JOVER, Andoni; MERCE VIDAL, Ramon; CALDENTEY FRONTERA, Francesc Xavier; RODRIGUEZ GARRIDO, Antonio, David; CARCELLER GONZALEZ, Elena; SALAS SOLANA, Jordi; WO2013/37960; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 100-54-9, Adding some certain compound to certain chemical reactions, such as: 100-54-9, name is Nicotinonitrile,molecular formula is C6H4N2, 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 100-54-9.

EXAMPLE 28 3-Pyridinecarboxamidine hydrochloride To a solution of 3-cyanopyridine (208 g, 2.0 mol) in methanol (100 ml) in an ice-bath was added sodium methoxide (11.2 g, 0.2 mol). The reaction mixture was stirred until all of the sodium methoxide had dissolved and was subsequently stoppered and placed in the refrigerator for 96 hours. Ammonium chloride (118 g, 2.2 mol) was then added and the reaction mixture was stirred in an ice-bath for 8 hours, followed by room temperature for 24 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was taken up in boiling ethanol (2 l), the solution was filtered and cooled to cause precipitation. The solid was collected by filtration and recrystallized in boiling n-propanol (1.4 l) to afford 153 g of a white solid. The filtrates were combined, concentrated in vacuo and the residue was recrystallized from n-propanol to afford 17.5 g of a white solid. The filtrate was once again concentrated in vacuo and the residue was recrystallized from n-propanol (500 ml) to afford 73 g of a white solid. The three crops were combined to afford 243.5 g (78%) of 3-pyridinecarboxamidine hydrochloride, m.p. 185-190 C. when dried at 60 C. in high vacuum.

According to the analysis of related databases, 100-54-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sterling Winthrop Inc.; US5294612; (1994); A;,
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. 17282-04-1, name is 2-Chloro-3-fluoropyridine. This compound has unique chemical properties. The synthetic route is as follows. COA of Formula: C5H3ClFN

A solution of 2-chloro-3-fluoropyridine (2 mmol) in anhydrous THF (10ml) was cooled to -780C. To this solution was added a solution of lithium diisopropylamide (LDA; 2.2 mmol) in hexane slowly at same temperature. After 2h at -780C, to the mixture was added trimethoxyborane (0.48ml) and stirred for 2h, followed by an addition of peracetic acid (0.72 ml; 32% in dilute acetic acid). The mixture was allowed to warm to O0C under stirring for Ih, then cooled to -2O0C, sodium dithionite (0.8g in 2ml water) was added dropwise. The mixture was extracted with ethyl acetate and the extract was dried and concentrated. The residue was purified by chromatography, eluting with 1:19 MeOH:DCM to give the expected product as a white solid (80%).

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, 17282-04-1, 2-Chloro-3-fluoropyridine.

Reference:
Patent; BTG INTERNATIONAL LIMITED; WO2009/103950; (2009); 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. 1214334-70-9, name is 5-Bromo-6-methoxypicolinic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-6-methoxypicolinic acid

To a solution of 5-bromo-6-methoxypyridine-2-carboxylic acid (500 mg, 2.15 mmol, 1.00 eq.) insulfuric acid (10 mL) in ice bath was added HNO3 (5 mL) dropwise. The resulting solution was allowed to stir at 60 C for 16 h. After being cooled to rt, the solution was poured into ice/water (20mL). The solids were collected by filtration to provide 3-amino-5-bromo-6-methoxypyridine-2- carboxylic acid as a light yellow solid (260 mg, 44%). LCMS (ES) [M-1] mlz 275.0.

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, 1214334-70-9, 5-Bromo-6-methoxypicolinic acid.

Reference:
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; YU, Ming; LI, Zhe; XU, Qing; YEE, Calvin; SETTI, Lina; SHAM, Hing; (188 pag.)WO2019/36384; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem