Month: September 2021

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.849937-96-8, name is 5-Bromo-2,4-dichloropyridine, molecular formula is C5H2BrCl2N, molecular weight is 226.8861, as common compound, the synthetic route is as follows.Recommanded Product: 5-Bromo-2,4-dichloropyridine

A solution of sodium methylate in methanol (0.95 ml, 0.90 mmol, 21%) was added dropwise to a flask containing 5-bromo-2,4,-dichloro-pyridine (0.75 g, 3.31 mmol) at 0 C. The reaction mixture was stirred at rt for 4 hours after which it was poured into ice-cold water and extracted with EtOAc. Organic phases were combined, washed with brine, dried (Na2S04), filtered and evaporated to dryness yielding 0.68 g of 5-bromo-2-chloro-4- methoxypyridine, NMR (DMSO-d6) delta: 8.43 (s, 1H), 7.32 (s, 1H), 3.99 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,849937-96-8, 5-Bromo-2,4-dichloropyridine, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 944401-77-8, 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.944401-77-8, name is 2-Amino-4-fluoropyridine, molecular formula is C5H5FN2, molecular weight is 112.105, as common compound, the synthetic route is as follows.

To a solution of 4-fluoropyridin-2-amine (2.5 g, 22.3 mmol) in acetonitrile (25 niL) was added TFA (0.85 mL, 11.16 mmol), S (5.5 g, 24.55 mmol) at 0 C and the reaction mixture was stirred at rt for 4 hours. After completion of the reaction, the reaction mixture was diluted with EtOAc (75 mL). The organic layer was washed with water (20 mL), dried (anhydrous NaPatent; RICHTER GEDEON NYRT.; ORION CORPORATION; HAIKARAINEN, Anssi; JOUBERT, Muriel; KAROLYI, Benedek; KAeSNAeNEN, Heikki; PASSINIEMI, Mikko; POHJAKALLIO, Antti; SZANTO, Gabor; VAISMAA, Matti; (97 pag.)WO2019/43635; (2019); 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.923169-37-3, name is 4-(Hydroxymethyl)picolinic acid, molecular formula is C7H7NO3, molecular weight is 153.14, as common compound, the synthetic route is as follows.Quality Control of 4-(Hydroxymethyl)picolinic acid

To a stirred solution of 4-(hydroxymethyl)picolinic acid 1 (461 mg, 3.012 mmol) in DMF (10 mL) was added diisopropylethylamine (0.8 mL, 4.518 mmol) and HATU (1.14 g, 3.012 mmol) at 0 C. After 20 min (1S,3R)-N1-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3- b]pyridin-3-yl)pyrimidin-4-yl)cyclohexane-1,3-diamine (Intermediate 12, enantiomer 2 (Ent- 2)) (750 mg, 1.506 mmol) was added and stirred the reaction mixture at room temperature for 16 h. After completion of the reaction, the mixture was diluted with ice cold water (100 mL) and filtered the precipitated solid to afford pure compound N-((1R,3S)-3-((5-fluoro-2-(5- fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl)amino)cyclohexyl)-4- (hydroxymethyl)picolinamide (Intermediate 23) (950 mg with 75% LCMS purity) as a brown solid. TLC system: 10% MeOH in dichloromethane; Rf: 0.6; LCMS (ESI): m/z 634.31(M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,923169-37-3, 4-(Hydroxymethyl)picolinic acid, and friends who are interested can also refer to it.

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

Adding a certain compound to certain chemical reactions, such as: 896722-50-2, 6-Chloro-1-(phenylsulfonyl)-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, 896722-50-2, blongs to pyridine-derivatives compound. HPLC of Formula: C13H9ClN2O2S

A solution of methylzinc chloride in THF (2 M) (9 mL, 12 mmol) was added to 6-chloro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.600 g, 2.05 mmol) and Pd(PPh3)4 (0.095 g, 0.08 mmol) in THF (30 mL). The mixture was refluxed for 40 h, cooled to 0 C., quenched with water and extracted with Et2O. The organic layer was concentrated and the residue was purified over a silica gel column eluting with EtOAc/hexane (1:5) to give N-protected 6-methyl-7-azaindole (0.495 g, 88%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,896722-50-2, its application will become more common.

Reference:
Patent; Hsieh, Hsing-Pang; Chao, Yu-Sheng; Liou, Jing-Ping; Chang, Jang-Yang; Tung, Yen-Shih; US2006/148801; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 89284-11-7, 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 89284-11-7, name is 5,6-Dibromopyridin-2-amine. This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5,6-dibromo-pyridin-2-ylamine (10 kg, 39.7 mol) A and methylcyclohexane (40 L) is heated to 65 C. At this temperature is added N,N- dimethylformamide dimethyl acetal (4.97 kg, 41.7 mol) over a period of 30 min rinsing with methylcyclohexane (10 L). The reaction mixture is heated to 100 C for 1 h or until the reaction is complete while removing 10 L of solvent under reduced pressure. Then, methylcyclohexane (20 L) is added and the mixture is cooled to about 60-55 C. Crystallization is initiated by addition of seeding crystals and the resulting suspension is cooled to 20 C over a period of 4 h and then stirred for additional 15 min at this temperature. The title product B is isolated by filtration, washed with methylcyclohexane (2 x 15 L) and dried under vacuum at 50 C. Yield 80 %. MS (ESI+) m/z = 306/308/310 [M+H]+.

According to the analysis of related databases, 89284-11-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LU, Guanghua; HUCHLER, Guenther; KRUEGER, Thomas; PANGERL, Michael; SANTAGOSTINO, Marco; DESROSIERS, Jean-Nicolas; (71 pag.)WO2017/198734; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 131747-69-8 , The common heterocyclic compound, 131747-69-8, name is 2-Fluoroisonicotinaldehyde, molecular formula is C6H4FNO, 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.

Example 132Preparation of 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a-((2-fluoropyridin- 4-yl)methylamino)-5a,5b,8,8,lla-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,ll,lla,llb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoic acid. Step 1. Preparation of methyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- ((2-fluoropyridin-4-yl)methylamino)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate.To a solution of methyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- amino-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate, HCl (318 mg, 0.548 mmol) in DCE (10 mL) was added glacial acetic acid (0.314 mL, 5.48 mmol), sodium acetate (67.4 mg, 0.822 mmol), 2-fluoropyridine-4-carboxaldehyde (206 mg, 1.644 mmol) and 4A molecular sieves. The reaction mixture was heated to 65 C for 18 h. To the reaction mixture was added sodium triacetoxyhydroborate (581 mg, 2.74 mmol) and the resulting mixture was heated to 65 C for 7.5 h, then the mixture was left at rt for 48 h. The reaction was diluted with DCM (50 mL) and washed with saturated aHC03 (20 mL). The aqueous layer was extracted with DCM (2 x 25 mL). The combined organic layer was dried over MgS04, filtered and concentrated. The resulting dark brown residue was dissolved in THF (3 mL) and MeOH (0.6 mL), filtered and purified by reverse phase preparative HPLC using HPLC method 3 to give methyl 4- ((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a-((2-fluoropyridin-4- yl)methylamino)-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)- 2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate, TFA (218.4 mg, 0.285 mmol, 52.0% yield) as a white solid. LCMS: m/e 653.4 (M+H)+, 2.69 min (method 6).

The synthetic route of 131747-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; REGUEIRO-REN, Alicia; LIU, Zheng; SWIDORSKI, Jacob; SIN, Ny; VENABLES, Brian Lee; SIT, Sing-Yuen; CHEN, Yan; CHEN, Jie; MEANWELL, Nicholas A.; WO2012/106190; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 96530-81-3, 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 96530-81-3 as follows.

To 3-iodo-lH-pyrazole (763 mg, 3.93 mmol) in DMSO (15 mL) at 0 C, was added sodium hydride (60% in mineral oil, 189 mg, 4.72 mmol). The reaction was warmed to 25 C and stirred for 60 min before 4-fluoro-2-methoxypyridine (500 mg, 3.93 mmol) was added. The reaction mixture was stirred at 90 C for 4.5 h before quenching by the addition of water. The reaction mixture was extracted with EtOAc. The combined organic extracts were dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 0-30% EtOAc in hexanes) to afford 4-(3- iodo-lH-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 301.97; found = 302.02 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,96530-81-3, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; HIRABAYASHI, Tomokazu; KATSUNO, Mika; SMITH, Cameron James; SHERER, Edward; CAMPEAU, Louis-Charles; BALKOVEC, James; GREENLEE, William John; LI, Derun; GUO, Liangqin; CHAN, Tin Yan; CHEN, Yi-Heng; CHEN, Yili; CHACKALAMANNIL, Samuel; TAN, John Qiang; WO2014/99694; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 18206-06-9, 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 18206-06-9, name is 2,6-Dimethylisonicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 2,6-dimethylpyridine-4-carbaldehyde (0.14 g, 1.00 mmol) in N,N-dimethyl acetamide (8 mL) were added 2-amino-5-(4-methyl-piperazin-1-ylmethyl)benzamide (0.25 g, 1.00 mmol), sodium hydrogensulfite (0.18 g, 1.20 mmol), and p-toluenesulfonic acid (0.057 g, 0.30 mmol). The reaction mixture was stirred at 115° C. for 20 hours under nitrogen, then cooled to room temperature. Solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane, washed with sat. NaHCO3, water, then brine, and dried over anhydrous sodium sulfate. Solvent was evaporated and the residue was purified by column chromatography (silica gel 230-400 mesh; 2-3percent 7 M ammonia in methanol and dichloromethane as eluent) to give the title compound. Yield: 0.035 g (9.6percent). MP 229-230° C. 1H NMR (400 MHz, CDCl3): delta 8.30 (br s, 1H), 7.88 (s, 2H), 7.84 (m, 2H), 3.66 (s, 2H), 2.72 (s, 6H), 2.50 (br s, 8H), 2.30 (s, 3H). MS (ES) m/z: 364.17 (M+1), 182.67 (100percent).

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 18206-06-9, 2,6-Dimethylisonicotinaldehyde.

Reference:
Patent; Resverlogix Corp.; Hansen, Henrik C.; (96 pag.)US9238640; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13472-60-1, 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. 13472-60-1, name is 3,5-Dibromo-2-methoxypyridine, molecular formula is C6H5Br2NO, 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.

Preparation 46-Bromo-2,2-dimethyl-2H-pyrano[2,3-b]pyridin-4(3H)-one[00153]A solution of 3,5-dibromo-2-methoxypyridine (1 1 .4 g, 42.7 mmol) in dry diethyl ether is cooled to -65 C and treated with BuLi (19 mL 2.5 M solution in hexane, 47.5 mmol) under argon atmosphere. The mixture is stirred at -70 C for 0.5 h. A solution of 3-methylbut-2-enal (3.44 g, 40.9 mmol) in dry THF (10 mL) is added to the mixture, and stirring is continued for another 0.5 h at -70 C. The reaction mixture is then warmed to r.t. and quenched with a saturated solution of sodium bicarbonate (100 mL). After extraction with DCM (3 x 100 mL) the combined organic layers are dried over Na2S04 and concentrated under reduced pressure to yield 1 -(5-bromo-2-methoxypyridin-3-yl)-3- methylbut-2-en-1 -ol (1 1 g, 95%).

According to the analysis of related databases, 13472-60-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERZ PHARMA GMBH & CO. KGAA; HENRICH, Markus; ABEL, Ulrich; MULLER, Sibylle; KUBAS, Holger; MEYER, Udo; HECHENBERGER, Mirko; KAUSS, Valerjans; ZEMRIBO, Ronalds; WO2012/52451; (2012); 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. 100367-39-3, name is 4-Bromo-2-methoxypyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 100367-39-3

General procedure: 5.1.12 2-[4-({[1-Methyl-4-(2-methylpyridin-4-yl)-1H-pyrazol-3-yl]oxy}methyl)phenyl]quinoline dihydrochloride (13a) Under argon gas atmosphere, to the mixture of 12 (200 mg, 0.45 mmol), 4-bromo-2-methylpyridine (156 mg, 0.91 mmol), and Na2CO3 (144 mg, 1.36 mmol) in DMF (2.0 mL) and water (0.87 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (PdCl2(dppf)·CH2Cl2, 22 mg, 0.027 mmol), and the mixture was stirred at 100 C for 1 h. After cooling at room temperature, the mixture was concentrated in vacuo, and the residue was purified by silica gel column chromatography (0-5% MeOH in CHCl3) to give a free from of the title compound, which was dissolved in MeOH and the mixture was treated with 4 M HCl/EtOAc. The precipitate formed was collected by filtration and washed with Et2O to give 13a (91 mg, 42%) as a colorless solid. 5.1.14 2-[4-({[4-(2-Methoxypyridin-4-yl)-1-methyl-1H-pyrazol-3-yl]oxy}methyl)phenyl]quinoline dihydrochloride (13c) Compound 13c was prepared from 12 and 4-bromo-2-methoxylpyridine in a manner similar to that described for compound 13a, with a yield of 51% as a colorless solid. 1H NMR (DMSO-d6) delta 3.79 (s, 3H), 3.95 (s, 3H), 5.47 (s, 2H), 7.29 (s, 1H), 7.41 (dd, 1H, J = 5.9, 1.3 Hz), 7.71-7.76 (m, 3H), 7.89-7.95 (m, 1H), 8.13 (d, 1H, J = 8.2 Hz), 8.17 (d, 1H, J = 5.9 Hz), 8.28 (d, 2H, J = 8.7 Hz), 8.33 (d, 2H, J = 8.4 Hz), 8.45 (s, 1H), 8.72 (d, 1H, J = 8.6 Hz); MS (ESI) m/z 423 [M+H]+; Anal. Calcd for C26H22N4O2·2.2HCl·3.5H2O: C, 56.10; H, 5.58; N, 10.06; Cl, 12.74. Found: C, 56.33; H, 5.68; N, 9.88; Cl, 12.52.

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, 100367-39-3, 4-Bromo-2-methoxypyridine.

Reference:
Article; Hamaguchi, Wataru; Masuda, Naoyuki; Miyamoto, Satoshi; Shiina, Yasuhiro; Kikuchi, Shigetoshi; Mihara, Takuma; Moriguchi, Hiroyuki; Fushiki, Hiroshi; Murakami, Yoshihiro; Amano, Yasushi; Honbou, Kazuya; Hattori, Kouji; Bioorganic and Medicinal Chemistry; vol. 23; 2; (2015); p. 297 – 313;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem