Day: April 20, 2022

Application of 197376-47-9, 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. 197376-47-9, name is Ethyl 6-Chloropyridine-3-acetate. A new synthetic method of this compound is introduced below.

Step 1: ethyl 2-(6-(pyrrolidin-1-yl)pyridin-3-yl)acetate A reaction mixture of ethyl (6-chloropyridin-3-yl)acetate (0.30 g, 1.5 mmol) (Asymchem, Cat. #110112), pyrrolidine (0.14 mL, 1.6 mmol and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.25 mL, 1.6 mmol) in dimethyl sulfoxide (2.0 mL) was stirred at 150 C. overnight. The mixture was diluted with water, and extracted with ethyl acetate (3*10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-40%) to afford the desired product (0.10 g, 28.4%). Analytic LCMS (M+H)+: m/z=235.2.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,197376-47-9, Ethyl 6-Chloropyridine-3-acetate, and friends who are interested can also refer to it.

Reference:
Patent; INCYTE CORPORATION; US2010/240671; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 709652-82-4, 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 709652-82-4 as follows.

To a microwave vial equipped with a stirbar was dissolve 2-amino-5-bromonicotinonitrile (0.087 g, 0.44 mmol) in anhydrous acetonitrile (4 mL). To the solution was added potassium acetate(0.086 g, 0.86 mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane (0.223 g, 0.86 mmol) and 1,1 ?-bis(diphenylphosphino)ferrocene-palladium(ll)dichloride (0.016 g, 0.022 mmol). The resulting mixture was microwaved at 150 C for 15 mm. To the mixture was added (1R,5S,6r)-6-(3-iodo- 1 -isopropyl- 1H-pyrazol-5-yl)-3-(oxetan-3-yl)-3-azabicyclo[3.1 .0]hexane (0.100 g, 0.26 mmol), 1M potassium carbonate (4 mL) and further1,1 ?-bis(diphenylphosphino)ferrocene-palladium(ll)dichloride (0.008 g, 0.011 mmol) and the resulting mixture was microwave at 110 C for 15 mm. The reaction mixture was diluted with 10 mL water and extracted with ethyl acetate (3 x 15 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to dryness in vacuo. This crude material was purified by RP-HPLC affording2-amino-5-(1 -isopropyl-5-((1R,5S,6r)-3-(oxetan-3-yl)-3-azabicyclo[3. 1 .0]hexan-6-yl)-1H-pyrazol-3-yl)nicotinonitrile (20.1mg, 21%): ?H NMR (400MHz, DMSO-d6) oe: 8.57 (s, 1H), 8.08 (s, 1H), 6.91(s, 2H), 6.35 (s, 1H), 4.73 -4.62 (m, 1H), 4.60-4.44 (m, 4H), 3.81 – 3.70 (m, 1H), 3.12 (d, J = 8.8Hz, 2H), 2.46-2.39 (m, 2H), 2.19-2.12 (m, 1H), 1.82- 1.76 (m, 2H), 1.42 (d, J = 6.5 Hz, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,709652-82-4, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 84539-34-4, 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 84539-34-4 as follows.

3-Bromo-5-(4-methoxy-phenyl)-pyhdin-4-ylamine (Intermediate compound 9) 25 To a solution of commercially available 4-amino-3,5-dibromopyridine (1 .500 g, 5.9545 mmol) in DME (40 ml) and water (20 ml), 4-methoxy phenyl boronic acid (0.995 g, 6.55 mmol) and sodium carbonate (1 .262 g, 1 1 .909 mmol) were added. The reaction mixture was degassed and kept under nitrogen atmosphere during the entire course of the reaction. Palladium (II) (bistriphenylphosphine)dichloride (0.209 g, 30 0.2977 mmol) was added and the resulting reaction mixture, heated at 9O0C for 4 hours, was worked up by addition of water and extraction with AcOEt. The organic phase, dried over anhydrous MgSO4, afforded upon evaporation a yellow gummy residue (1 .650 g), which eluted through silica gel with 20% AcOEt in hexane gave 1 .500 g (-54% yield) of the pure title compound as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,84539-34-4, its application will become more common.

Reference:
Patent; NEUROSEARCH A/S; WO2009/112461; (2009); 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. 1033610-45-5, name is 4-Bromo-3,5-dimethoxypyridine, molecular formula is C7H8BrNO2, 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: 1033610-45-5

4-bromo-3,5-dimethoxypyridine of structural formula 2 (440 mg, 2.0 mmol, 1.0 equiv.) was dissolved in 2 mL of an acetic acid solution of 33% by mass of hydrogen bromide. Heat to 130 C and react for 24 hours. After the reaction was completed, a 10% aqueous sodium hydrogencarbonate solution was added. After the workup, 335 mg of the crude product was obtained. Since the structural formula 3 is easily decomposed in the air, the crude product was used directly in the next reaction.

With the rapid development of chemical substances, we look forward to future research findings about 1033610-45-5.

Reference:
Patent; Chongqing University; Li Yang; Chen Di; (11 pag.)CN109836446; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13958-93-5, 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 13958-93-5, name is 3,5-Dichloroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

3,5-Dichloroisonicotinic acid (5 g) was suspended in 12 mL of thionyl chloride and stirred under reflux for 18 hours. The reaction mixture was concentrated. The resulting acid chloride (1.30 g, 6.2 mmol) was dissolved in 5 mL of 1,4-dioxane at 0C. The reaction mixture was stirred at 0C for 15 minutes and allowed to warm to room temperature and stirred for an additional 30 minutes. It was then cooled to 0C and carefully quenched with 15 mL of water. The reaction mixture was extracted with CH2Cl2 and the combined organic layers were dried with Na2SO4 and concentrated under reduced pressure. The resulting crude product was purified by chromatography (3: 1 hexanes/EtOAc) to afford 650 mg of the alcohol intermediate. This alcohol intermediate was dissolved in 1 mL of thionyl chloride and stirred under reflux for an hour. The resulting reaction mixture was cooled to room temperature and concentrated under reduced pressure to afford the chloromethyl pyridine derivative as a yellow solid.

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 13958-93-5, 3,5-Dichloroisonicotinic acid.

Reference:
Patent; BIOGEN IDEC MA INC.; WO2004/92170; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 95652-81-6, 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 95652-81-6, name is 6-Chloro-2-methoxynicotinaldehyde. This compound has unique chemical properties. The synthetic route is as follows.

Step-2: Preparation of 6-chloro-2-methoxypyridine-3-carboxylic acid:-To a cold solution of 6-chloro-2-methoxypyridine-3-carbaldehyde (15.0 g, 0.087 mol) in acetone was added sulphamic acid (10.1 g, 0.105 mol) and sodium chlorite (9.4 g, 0.105 mol) at 0C. The reaction mass was stirred at room tempreture for 2 hours. Acetone was removed under vaccume and water was added to the reaction mass. The reaction mass fwas stirred for 1 hour and filtered to afford 15.0 g of desired product. ‘HNMR (DMSO- d6): delta 3.91 (s, 3H), 7.18 (d, J = 7.8 Hz, 1H), 8.14 (d, J = 7.8 Hz, 1H,), 13.15 (br s, 1H); MS [M+H]+ : 190.18.

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 95652-81-6, 6-Chloro-2-methoxynicotinaldehyde.

Reference:
Patent; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; GAJERA, Jitendra Maganbhai; NARAYANA, Lakshminarayana; KHAIRATKAR-JOSHI, Neelima; KATTIGE, Vidya Ganapati; WO2012/110860; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic 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, Recommanded Product: 167837-43-6, blongs to pyridine-derivatives compound. Recommanded Product: 167837-43-6

To a solution OF METHYL- (2-METHYLBENZOFURAN-3-YLMETHYL)-AMINE (176 mg, 1.0 mmol), 3- (6-AMINO-PYRIDIN-3-YL)-ACRYLIC acid (150 mg, 0.91 mmol), HOBt (135 mg, 1.0 mmol) and diisopropylethylamine (0.46 mL, 2.7 mmol) in DMF (10 mL) was added EDC (209 mg, 1. 1 mmol). The yellow solution was stirred overnight at room temperature. The reaction mixture was cooled to 0 C then treated with H20 (40 mL) to form a precipitate. The precipitate was filtered, washed with H20 (20 mL) then with a 10% EtOAc: hexanes solution (10 mL). The solid was dissolved in a 10% MeOH: CH2Cl2 solution (20 mL), cooled to 0 C then treated with 2 mL of a 1.0 M HCl in ET20. After stirring for 10 minutes, the yellow solution was concentrated to dryness then triturated with Et2O (20 mL). The title compound was collected and dried under vacuo to yield the title compound (76.9%) as a mixture of amide rotamers. 1H NMR (300 MHz, DMSO-D6) 8 8. 41-8. 33 (m, 3H), 7.58- 7.02 (m, 6H), 4.93 and 4.74 (2 x s, 2H), 3.05 and 2.82 (2 x s, 3H), 2.53 and 2.48 (2 x s, 3H); MS (ESI) NALE 322 (M+ H) +.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,167837-43-6, (E)-3-(6-Aminopyridin-3-yl)acrylic acid, and friends who are interested can also refer to it.

Reference:
Patent; AFFINIUM PHARMACEUTICALS, INC.; WO2004/52890; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 823221-93-8, 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. 823221-93-8, name is 5-Bromo-2-chloro-4-(trifluoromethyl)pyridine, molecular formula is C6H2BrClF3N, 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.

General procedure: To a solution of halogenopyridine (1.0 eq) in indicated solvent at rt was added hydrazinehydrate (1-10 eq.). Reaction mixture was stirred at the indicated temperature for theindicated time. Solvents were concentrated under vacuum. Water or saline solution was then added Precipitate that formed was filtered off, washed with water and dried under vacuum yielding 2-hydrazinylpyridi ne.

According to the analysis of related databases, 823221-93-8, the application of this compound in the production field has become more and more popular.

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

Electric Literature of 64951-08-2, 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 64951-08-2 as follows.

Step (d) N-[4-(l-cyclopentyl-6-fluoro-2,4-dioxo-l,4-dihydropyrido[2,3-d]pyrimidin-3(2H)-yl)cyclohexyl]imidazo[l,2-a]pyridine-2-carboxamide To a mixture of imidazo[l,2-a]pyridine-2-carboxylic acid (89mg, 0.55mmol), HATU(220mg, 0.55mmol), HOAT (75mg, 0.55mmol) and 3-(4-aminocyclohexyl)-l-cyclopentyl-6-fluoro-pyrido[2,3-d]pyrimidine-2,4(lH,3H)-dione hydrochloride (176mg, 0.46mmol) inN-methylpyrrolidinone (10ml) was added ethyl-di-isopropylamine (0.31ml, 1.81mmol) over a period of 20 seconds. Stirring was continued at ambient temperature for 3 days and the reaction mixture was poured onto water. The obtained solid was filtered, dried on the sinter, dissolved in chloroform and adsorbed onto silica gel. Flash chromatography using a mixture of petrol ether and ethyl acetate yielded the title compound (55mg, 24%) as a colourless solid.1H NMR (300MHz, DMSO-J*): delta 8.77 (IH, d); 8.60 (IH, ddd); 8.40 (IH, s); 8.25 (IH, dd); 7.78 (IH, d); 7.68 (IH, d); 7.38 (IH, dd); 7.00 (IH, dd); 5.80 (IH, p); 4.84 (IH, bt);2.89 (IH, bs); 2.50 – 2.70 (2H, bm); 2.04 – 2.22 (2H, bd); 1.41 – 2.04 (12H, m).APCI-MS m/z: 491 [MH+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,64951-08-2, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/84223; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 13466-35-8, 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.13466-35-8, name is 3-Chloro-2-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.54, as common compound, the synthetic route is as follows.

EXAMPLE 1 3-Chloro-5-octyl-2-(4-octyloxyphenyl)pyridine 10.5 ml (203.0 mmol) of bromine are added dropwise at 0 C. to 23.9 g (184.5 mmol) of 3-chloro-2-hydroxypyridine in 240 ml of dimethylformamide, and the mixture is stirred at room temperature for 2 hours. 200 ml of water are subsequently added, and 30 g of sodium sulfite in 100 ml of water are added dropwise. After 15 minutes, the mixture is extracted three times with 200 ml of dichloromethane in each case, the combined organic phases are dried over sodium sulfate and filtered, and the filtrate is evaporated to dryness, giving 36.58 g of 5-bromo-3-chloro-2-hydroxypyridine. STR13 m.p.: 168 C. (decomp.)

The chemical industry reduces the impact on the environment during synthesis 13466-35-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoechst Aktiengesellschaft; US5629428; (1997); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem