Tag: M.W:100-200

Adding a certain compound to certain chemical reactions, such as: 22282-99-1, 4-Bromo-2-methylpyridine, 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, 22282-99-1, blongs to pyridine-derivatives compound. Product Details of 22282-99-1

[0566] Step 1: ethyl 2-(4-bromopyridin-2-yl)acetate – To a stirred solution of 4-bromo-2-methylpyridine (1.2 g, 4.93 mmol, 1.0 eq) in THF (15 mL), was added diethyl carbonate (0.698 mL, 5.92 mmol, 1.2 eq) and the mixture stirred at -78C under nitrogen atmosphere. LDA(2′-78C for 2h. The reaction was then quenched with saturated sodium chloride solution and the product extracted with EtOAc (2′-(4-bromopyridin-2-yl)acetate (0.500 g, 30%) as a pale yellow liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22282-99-1, its application will become more common.

Reference:
Patent; CAPULUS THERAPEUTICS, LLC; GREEN, Michael John; HART, Barry Patrick; (341 pag.)WO2019/148125; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 83766-88-5, 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. 83766-88-5, name is 2-(tert-Butoxy)pyridine, molecular formula is C9H13NO, 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.

Carboxylic acid (0.2 g, 1.64 mmol), tert-butoxypyridine (0.33 g, 2.21 mmol) and boron trifluoride diethyl etherate (0.31 g, 2.21 mmol) in dry PhCH3 (2 mL) were added to a 20-ml vial. The reaction mixture was then allowed to stir at room temperature for 30 min before quenching with anhydrous NaHCO3. The reaction mixture was diluted with ethyl acetate (30 mL), then washed with water (20 mL), followed by brine (20 mL). The organic layer was dried over anhydrous sodium sulfate and carefully concentrated under reduced pressure. The resulting residue was then purified by flash column chromatography on silica gel with 0:4 to 1:4 dichloromethane/hexane as eluent to yield the desired product 5a as a colorless oil.

According to the analysis of related databases, 83766-88-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; La, Minh Thanh; Kim, Hee-Kwon; Tetrahedron; vol. 74; 27; (2018); p. 3748 – 3754;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1256808-59-9 ,Some common heterocyclic compound, 1256808-59-9, molecular formula is C7H6FNO2, 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.

To a solution of 5-fluoro-3-methylpicolinic acid (40.0 mg, 258 mumol, Eq: 1.2) in methanol (3.00 ml) was added at 0 C 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) (83.3 mg, 301 mumol, Eq: 1.4), the colorless solution was stirred at 0 C for 30 min, then a solution of (3R,4aS)-3-(5-amino-2-fluoro-phenyl)-3-methyl-4a-oxo-3,4,6,7,8,9-hexahydro-4alambda6-thia-2,5,9a-triaza-benzocyclohepten-1-ylamine (70 mg, 215 mumol, Eq: 1.00) in methanol (5.00 ml) was added dropwise via syringe and the reaction mixture was stirred at 23 C for 4 h. Extracted with ethyl acetate and sat. NaHCO3-sol. plus brine, dried organic layer over Na2SO4. Filtration and removal of the solvent in vacuum left a brown foam which was purified by flash chromatography (NH2-silica gel, 20 g, 0% to 100% EtOAc in heptane) to give the 5-fluoro-3-methyl-pyridine-2-carboxylic acid [3-((3R,4aS)-1-amino-3-methyl-4a-oxo-3,4,6,7,8,9-hexahydro-4alambda6-thia-2,5,9a-triaza-benzocyclohepten-3-yl)-4-fluoro-phenyl]-amide (29 mg, 62.7 mumol, 29.1 % yield) as a white solid. MS (ISP): m/z = 463.2 [(M+H)+]

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 1256808-59-9, 5-Fluoro-3-methylpicolinic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GUBA, Wolfgang; HAAP, Wolfgang; KUGLSTATTER, Andreas; PETERS, Jens-Uwe; OBST SANDER, Ulrike; SCHNIDER, Christian; WERMUTH, Roger; WOLTERING, Thomas; WO2015/91595; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14916-65-5, 6-Nitropyridin-3-amine, 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, SDS of cas: 14916-65-5, blongs to pyridine-derivatives compound. SDS of cas: 14916-65-5

Dichloromethane 10 ml, 2-nitro 5-aminopyridine (200 mg, 1.4 mmol) starting material 1 and ethyl 4-bromo-2-oxo-butyrate (280 ml, 1.4 mmol) were added to a 50 ml reaction flask at room temperature. The magnetic stirring reaction was performed for 1 to 2 hours, and the solvent was concentrated under reduced pressure. The residue was dissolved with 10 ml of ethanol and specifically ethanol, and the mixture was heated under reflux for 3 h. The reaction was completely checked by TLC.The reaction solution was allowed to cool to room temperature and concentrated under reduced pressure to remove the ethanol.The residue was washed with saturated sodium hydrogencarbonate solution and the aqueous layer was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate overnight, suction filtered and concentrated, and the residue was separated using silica gel column chromatography to give Intermediate 2 as a yellow solid.MS calculated 235, found 236 [M+l].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,14916-65-5, 6-Nitropyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; Wuxi Fuqi Pharmaceutical Co., Ltd.; Wang Tao; Wang Binbin; Wang Qinglin; Sun Yilin; You Benjia; Cao Na; (9 pag.)CN107573364; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 147071-00-9, 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 147071-00-9 as follows.

To a stirred solution of methyl 1 AY-pyrrolo[2,3-c]pyridine-5-carboxylate (15.Og, 85.1 mmol) in DMF (120 mL) at 1O0C under a nitrogen atmosphere was added sodium hydride (3.75 g, 60% in mineral oil, 93.7 mmol) in three portions over 5 min. The slurry became a homogeneous solution. After 130 min at 10 0C, 4- fluorobenzyl bromide (0.6Og, 2.89 mmol) was added at such a rate that the temperature did not exceed 15 0C. The resulting mixture was stirred for 2.5 hours at ambient temperature, quenched with water (12OmL), and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were washed with water (2 x 30 mL), dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by flash chromatography. Elution with hexane:ethyl acetate (2:1) provided the title compound as a white solid (21.3 g, 88% yield). 1H NMR (300 MHz, DMSO-D6) delta, ppm: 3.84 (s, 3H), 5.59 (s, 2H), 6.73 (d, J=2.Q Hz, 1H), 7.15 (t, J=8.9 Hz, 2H), 7.34 (dd, J=8.3, 5.7 Hz, 2H), 7.87 (d, J=2.8 Hz, 1 H), 8.3 (s, 1 H), 8.97 (s, 1 H). LCMS (APCi, M+H+): 285.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,147071-00-9, its application will become more common.

Reference:
Patent; PFIZER INC.; WO2006/27694; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 96630-88-5, Adding some certain compound to certain chemical reactions, such as: 96630-88-5, name is 4-Chloro-3-hydroxypyridine,molecular formula is C5H4ClNO, 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 96630-88-5.

Step A: Preparation of 4-Chloro-3-methoxypyridine. To a cold solution of 4-chloropyridin-3-ol (200 mg, 1.544 mmol), triphenylphosphine (0.810 g, 3.088 mmol), and MeOH (0.125 mL, 3.088 mmol) in THF (5 mL) was slowly added diisopropyl azodicarboxylate (0.610 mL, 3.088 mmol). The reaction was stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure and the residue was triturated with EtOAc to precipitate triphenylphosphine oxide. The solid was removed by filtration and the filtrate was concentrated under reduced pressure and purified by column chromatography to give the title compound (89.4 mg, 0.623 mmol, 40.3%) (purity was about 58 wt%) as a brown oil. LCMS m/z = 144.2 [M+H]+; lU NMR (500 MHz, CDC13) delta ppm 4.00 (s, 3H), 7.32 (d, J = 5.04 Hz, 1H), 8.17 (d, J = 4.41 Hz, 1H), 8.30 (s, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 96630-88-5, 4-Chloro-3-hydroxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; JONES, Robert, M.; BUZARD, Daniel, J.; HAN, Sangdon; KIM, Sun, Hee; LEHMANN, Juerg; WO2012/170702; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 628691-93-0, 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 628691-93-0, name is 2-Chloro-3-fluoroisonicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 1. 3-fluoro-2-vinylisonicotinic acidA solution of 2-chloro-3-fluoroisonicotinic acid (1.50 g, 8.55 mmol, Matrix), dibutyl vinylboronate (2.82 mL, 12.8 mmol, Aldrich), and potassium carbonate (1.42 g, 10.25 mmol) in N,N-dimethylacetamide (9 mL) and water (3 mL) was degassed by bubbling a stream of nitrogen through the solution for 20 minutes.Tetrakis(triphenylphosphine)palladium(0) (0.59 g, 0.51 mmol) was added and the mixture was similarly degassed for a further 10 minutes. The reaction vessel was sealed and heated in the microwave for 25 minutes at 135 C. The reaction mixture was filtered and purified using preparative HPLC (UV-detection) eluting with a gradient ofH20/MeCN containing 0.1% TFA. This reaction was run again on the same scale and the product of both runs were pooled. Solvent was removed from the eluent containing desired product in vacuo (1.3 g, 46%). 1H NMR (300 MHz, CD3OD): delta 8.45 (d, 1H), 7.69 (dd, 1H), 7.07 (ddd, 1H), 6.44 (dd, 1H), 5.65 (dd, 1H); 19F NMR (282 MHz, CD3OD): delta -129.64 (d, IF); LCMS (M+H)+: 167.9.

According to the analysis of related databases, 628691-93-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INCYTE CORPORATION; RODGERS, James D.; SHEPARD, Stacey; ZHU, Wenyu; SHAO, Lixin; GLENN, Joseph; WO2012/68450; (2012); 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.1211541-93-3, name is 5-Fluoro-2-methoxypyridin-3-amine, molecular formula is C6H7FN2O, molecular weight is 142.13, as common compound, the synthetic route is as follows.name: 5-Fluoro-2-methoxypyridin-3-amine

To a solution of XII-1 (0.50 g, 1 .97 mmol) in pyridine (10 mL) was added X-1 (0.18 g, 1 .25 mmol) and DMAP (0.012 g, 0.09 mmol). The reaction mixture was heated at 80 C for 16h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated under vacuum. The residue was diluted with H20 (100 mL), 1 N HCI (50 mL) and extracted with EtOAc (100 mL). The organic layer was separated, dried over anhydrous Na2S04 and concentrated under vacuum. The crude obtained was purified by column chromatography (silica, 100-200 mesh, 40% EtOAc in hexane) to afford 6-chloro-N-(2,5-difluoropyridin-3-yl)-1H-indole-3-sulfonamide 1-1 (0.05 g) as an off-white solid. (1207) Yield: 7%. (1208) Basic LCMS Method 1 (ES ): 342 (M-H)-, 97% purity. (1209) 1H NMR (400 MHz, DMSO-cfe) d 7.25 (dd, J=8.31 , 1.47 Hz, 1 H), 7.54 (s, 1 H), 7.71-7.81 (m, 2H), 7.89 (s, 1 H), 8.16 (d, J=2.93 Hz, 1 H), 10.73 (brs, 1 H), 12.22 (brs, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211541-93-3, 5-Fluoro-2-methoxypyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; UCB PHARMA GMBH; PEGURIER, Cecile; PROVINS, Laurent; CARDENAS, Alvaro; LEDECQ, Marie; MUELLER, Christa E.; HOCKEMEYER, Joerg; EL-TAYEB, Ali; BOSHTA, Nader; RASHED, Mahmoud; (165 pag.)WO2019/243303; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 122306-01-8, 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. 122306-01-8, name is (6-Bromopyridin-3-yl)methanol. A new synthetic method of this compound is introduced below.

Step 1A solution of (beta-bromopyridin-3-yl) methanol (2.39 g) described in a reference (Ellingboe, J. W. et al. J. Med. Cheralpha. 1994, 37, 542-550.) in THF (65 mL) was ice-cooled, thionyl chloride (4.64 mL) was added, and the mixture was stirred at 0C for 6 hr. The reaction mixture was concentrated under reduced pressure. Toluene was added and the mixture was concentrated again, and dried under reduced pressure to give 2-bromo-5- (chloromethyl) pyridine hydrochloride (2.54 g) as a brown solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,122306-01-8, (6-Bromopyridin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/119880; (2009); 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.55052-27-2, name is 6-Chloro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5ClN2, molecular weight is 152.581, as common compound, the synthetic route is as follows.Computed Properties of C7H5ClN2

4 g (0.03 mol) of aluminum trichloride, 3 ml of dichloromethane and 3.6 g (0.02 mol), i.e. 2.23 ml, of trichloroacetyl chloride are placed in a round-bottomed flask with a condenser, a magnetic stirrer and a calcium chloride guard tube, and the mixture is stirred at room temperature for 30 minutes. 1.52 g (0.01 mol) of 6-chloro-1H-pyrrolo[2,3-b]pyridine are added portionwise and the mixture is refluxed for 3 hours. While cooling in an ice bath, 50 ml of ice are added to the flask and the mixture is stirred vigorously for 30 minutes. A pasty mass is obtained, which is separated from the aqueous phase by decantation. The product is used directly in the next step.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55052-27-2, 6-Chloro-1H-pyrrolo[2,3-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; SANOFI-AVENTIS; US2005/182062; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem