Month: April 2022

Reference of 89488-30-2, 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. 89488-30-2, name is 5-Bromo-3-methylpyridin-2(1H)-one, molecular formula is C6H6BrNO, 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.

EXAMPLE 11B 5-bromo-2-chloro-3-methylpyridine The product from Example 11A (4.1 g, 221.8 mmol) in DMF (40 mL) was treated with phosphorus oxychloride (10 g, 65.4 mmol) dropwise at 0 C. After heating at 120 C. for 2 hours, the mixture was cooled and poured onto ice/water. The mixture was made basic with NH4OH, filtered, and the filtercake washed with ice water. The obtained solid was dissolved in dichloromethane (100 mL), washed with brine, and dried (MgSO4). The dried solution was filtered through a pad of silica using dichloromethane and the filtrate concentrated to provide the title compound as a white solid (3.48 g, 78% yield): 1H NMR (CDCl3, 300 MHz) delta 2.39 (s, 3H), 7.70 (m, 1H), 8.31, d, J=3 Hz, 1H).

According to the analysis of related databases, 89488-30-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Schrimpf, Michael R.; Tietje, Karin R.; Toupence, Richard B.; Ji, Jianguo; Basha, Anwer; Bunnelle, William H.; Daanen, Jerome F.; Pace, Jennifer M.; Sippy, Kevin B.; US2002/19388; (2002); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 898746-42-4, 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. 898746-42-4, name is 6-Fluoro-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5FN2, 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 17Synthesis of l-cyclopropyl-6-fluoro-lH-pyrrolo[2,3-b]pyridine.To a solution of 6-fluoro-lH-pyrrolo[2,3-b]pyridine (6.2 g, 45.55 mmol) in dryDCM (250 mL) is added cyclopropylboronic acid (7.82 g, 91.09 mmol), followed by cupric acetate (8.36 g, 45.55 mmol), sodium carbonate (9.65 g, 91.09 mmol) and 2,2′- bipyridine (7.1 1 g, 45.55 mmol). The resulting mixture is stirred and heated at 50C for 15h. The mixture is cooled to room temperature and further cupric acetate (4.18 g, 22.77 mmol) and sodium carbonate (2.41 g, 22.77 mmol) are added, followed bycyclopropylboronic acid (1.96 g, 22.77 mmol). The mixture is stirred and heated at 50C for a further 15h when further cupric acetate (1.5 g, 8.25 mmol) and cyclopropylboronic acid (1.49 g, 17.34 mmol) are added. The mixture is stirred at room temperature for 4 days and then poured onto sat. aq. NH4C1, diluted with water and extracted with DCM. The organic layers are combined, washed with brine, dried (magnesium sulphate) and concentrated in vacuo to give a green oil, which is purified by column chromatography on silica, eluting with DCM, to give the title compound (2.03 g, 11.52 mmol). MS (m/z): 177 (M+l). Unreacted 6-fluoro-lH-pyrrolo[2,3-b]pyridine is also recovered (3.012g, 22.1 mmol). MS (m/z): 137 (M+l).

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 898746-42-4, 6-Fluoro-1H-pyrrolo[2,3-b]pyridine.

Reference:
Patent; ELI LILLY AND COMPANY; LAMAS-PETEIRA, Carlos; RICHARDS, Simon, James; SAPMAZ, Selma; WALTER, Magnus, Wilhelm; WO2012/74769; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 61494-55-1, 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. 61494-55-1, name is 2-(2-Chloropyridin-3-yl)acetic acid. A new synthetic method of this compound is introduced below.

Acetyl chloride (0.651 mL, 9.18 mmol) was added to a suspension of (2- chloropyridin-3-yi)acetic acid (1117) (1.048 g, 6.108 mmol) in MeOH (30 mL). The mixture was heated at reflux for 20 hours. The voiatiles were removed in vacuo and the residue partitioned between DCM (100 mL) and sat. NaHC03 (100 mL). The layers were separated and the aqueous layer extracted with DCM (2×100 mL). The combined organic layers were washed with brine (100 mL), dried (Na2S04) and the solvent removed under reduced pressure to yield an oil which was purified by column chromatography on silica gel (0-40% EtOAc in petroleum benzine 40-60 C) to afford the title compound (1118) (0.863 g, 76%) as a pale yellow oil; 1H NMR (400 MHz, d6~ DMSO) delta 8.34 (dd, J = 4.8, 1.9 Hz, 1 H), 7.83 (dd, J = 7.5, 1.9 Hz, 1 H), 7.43 (dd, J = 7.5, 4.8 Hz, 1 H), 3.86 (s, 2H), 3.65 (s, 3H). LC S Method C: rt 5.04 min; m/z 186 [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,61494-55-1, its application will become more common.

Reference:
Patent; CANCER THERAPEUTICS CRC PTY LTD; DEVLIN, Mark Graeme; STREET, Ian Philip; TONG, Warwick Bonner; WO2014/27199; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 880870-13-3, Adding some certain compound to certain chemical reactions, such as: 880870-13-3, name is 5-Bromo-2-chloro-4-methoxypyridine,molecular formula is C6H5BrClNO, 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 880870-13-3.

Step B: 6-Chloro-4-methoxypyridine-3-carbonitrile: A solution of 5-bromo-2-chloro-4- methoxypyridine (5.0 g, 22.48 mmol) in DMF (80 mL) was purged with nitrogen for 15 min. At this point, Zn(CN)2 (3.96 g, 33.7 mmol) and Pd(Ph3P)4 (2.60 g, 2.25 mmol) were added successively. The resulting suspension was stirred at 95 C for 12 h under nitrogen. The reaction mixture was cooled to ambient temperature, and filtered to remove inorganic solid. The solvent (DMF) was evaporated to provide the crude residue, which was purified on silica gel and eluted with 0-30% ethyl acetate / hexanes to afford the product.

According to the analysis of related databases, 880870-13-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alexander; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda, K.; SUZUKI, Takao; WO2015/100147; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 97966-00-2 ,Some common heterocyclic compound, 97966-00-2, molecular formula is C5H2BrCl2N, 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 5-bromo-2,3-dichloropyridine (29) (11.7 g, 51.6 mmol) was added HBr (5M in AcOH) (51.6 ml, 258 mmol) at room temperature. Then the reaction mixture was heated to 70 C. After being stirred for 7 hrs at 70 C., the reaction mixture was diluted with ethyl acetate, quenched with H2O and extracted with ethyl acetate. The resulting organic layer was washed with 1M NaOH, dried over over Na2SO4 and concentrated in vacuo. The residue was recrystallized from hexane-ethyl acetate to afford 11.2 g of the desired product (41) in 80% yield as a white solid. 1H-NMR (DMSO-d6) delta: 8.55 (1H, s), 8.49 (1H, s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97966-00-2, its application will become more common.

Reference:
Patent; SHIONOGI & CO., LTD.; Kurose, Noriyuki; Iso, Yasuyoshi; Yamaguchi, Naoko; Shao, Bin; Tafesse, Laykea; Zhou, Xiaoming; Yu, Jianming; US9156830; (2015); B2;,
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.1254473-66-9, name is 1-(3,5-Dichloropyridin-4-yl)ethanol, molecular formula is C7H7Cl2NO, molecular weight is 192.04, as common compound, the synthetic route is as follows.Computed Properties of C7H7Cl2NO

(30eq) was added to 30 ml of anhydrous THF and 327 mg (3.0 eq) of 60% NaH was added. After 30 min of activation, 400 mg of the starting material 17 was added and the reaction was complete after 12 hours of refluxing. Water and acetic acid The combined organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was dried to give brown oil 18 (420 mg) in 57.3% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1254473-66-9, 1-(3,5-Dichloropyridin-4-yl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; SICHUAN BAILI PHARMACEUTICAL CO LTD; WU, YONG; ZHU, YI; HAI, LI; WANG, YIXI; LI, JIE; (23 pag.)CN105906621; (2016); A;,
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.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.Computed Properties of C6H4BrN3

To a solution of 2-amino-5-bromonicotinonitrile (1.4 equiv.) in toluene and ethanol (2.5:1) was added N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)phenyl)-3-(trifluoromethyl)benzamide (1.0 equiv.), Pd(PPh3)4 (0.1 equiv.) and aqueous potassium carbonate (3M, 3.0 equiv.). The reaction was heated in the microwave at 120 C for 40 min. The organic layer was separated and concentrated to dryness under vacuo. The residue was dissolved in DMSO and purified via reverse phase HPLC. The pure fractions were lyophilized to give N-(3-(6-amino-5-cyanopyridin-3-yl)-4-methylphenyl)-3- (trifluoromethyl)benzamide as the TFA salt in 48% yield. 1H NMR (400 MHz, DMSOd6) G 10.45 (s, 1H), 8.30 (s, 1H), 8.25 (d, J=2.0, 1H), 8.23 (d, J=2.0, 1H), 7.97 (d, J=8.0, 1H), 7.95 (d, J=4.0, 1H), 7.79 (t, J=8.0, 1H), 7.72 (dd, J=8.0, 2.0, 1H), 7.61 (d, J=4.0, 1H), 7.30 (d, J=12.0, 1H), 2.23 (s, 3H). LCMS (m/z) (M+H) = 397.1, Rt = 0.91 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,709652-82-4, 2-Amino-5-bromonicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; BARSANTI, Paul Andrew; BURGER, Matthew T.; LOU, Yan; NISHIGUCHI, Gisele A.; POLYAKOV, Valery Rostislavovich; RAMURTHY, Savithri; SUBRAMANIAN, Sharadha; TAFT, Benjamin R.; TANNER, Huw Rowland; WAN, Lifeng; (180 pag.)WO2016/38583; (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.849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, molecular formula is C8H5BrN2O2, molecular weight is 241.04, as common compound, the synthetic route is as follows.Application In Synthesis of 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

To a solution of 5-bromo-lH-pyrrolo [2,3-b] pyridine-3-carboxylic acid (600 mg, 2.49 mmol)Of N, N-dimethylformamide (20 mL)To the solution was added 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (1.44 g, 7.43 mmol)1-hydroxybenzotriazole (1.01 g, 7.46 mmol) and2-isopropylamine (1.27 mL, 14.90 mmol),Stir overnight at room temperature.Saturated brine (20 mL) was added,Dichloromethane (15 mL x 3)Dried over anhydrous sodium sulfate, the solvent was removed,The concentrate was subjected to column chromatography (eluent: petroleum ether / ethyl acetate (v / v) = 5/1) to give the product as360 mg of a brown solid, yield: 51.3%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); 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. 22282-70-8, name is 2-Fluoro-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows. Recommanded Product: 2-Fluoro-4-iodopyridine

A solution of 2-fluoro-4-iodopyridine (10.00 g, 43.50 mmol) and ammonia (10 mL) in DMSO (20 mL) was stirred at 100 C for 40 h.Water (100 mL) was added to the reaction solution, and a solid was precipitated. The brown solid compound 10a (8.62 g, 90%) was obtained by filtration

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, 22282-70-8, 2-Fluoro-4-iodopyridine.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD; MA, CUNBO; GAO, PANLIANG; CHU, JIE; WU, XINPING; WEN, CHUNWEI; KANG, DI; BAI, JINLONG; PEI, XIAOYAN; (171 pag.)TW2019/25186; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, 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, Safety of 2-(Bromomethyl)-6-methoxypyridine, blongs to pyridine-derivatives compound. Safety of 2-(Bromomethyl)-6-methoxypyridine

A room temperature solution of 4-(6-(piperazin- 1 -yl)pyridin-3 -yl)-6-( 1 H-pyrazol-4- yl)pyrazolo[1,5-a]pyridine-3-carbonitrile bis(2,2,2-trifluoroacetate) (Example 698, Step 1; 6 mg, 0.0162 mmol) in dry DMA (900 tL) was treated sequentially with TEA (22.6 tL, 0.162 mmol) and 2-(bromomethyl)-6-methoxypyridine (9.82 mg, 0.0486 mmol). The reaction mixture was stirred overnight at room temperature before introducing additional TEA (1 tL, 0.01 mmol) and 2-(bromomethyl)-6-methoxypyridine (2mg, 0.01 mmol). The reaction mixture was stirred at room temperature until LCMS indicated the reaction was complete. The reaction mixture was directly purified by Cl 8 reverse-phase chromatography (15-80% ACN/water with 0.1% formic acid as the gradient eluent) to cleanly afford the title compound (2.5 mg, 51% yield). MS (apci) m/z = 492.2(M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156094-63-2, 2-(Bromomethyl)-6-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; ARRAY BIOPHARMA, INC.; ANDREWS, Steven W.; BLAKE, James F.; CHICARELLI, Mark J.; GOLOS, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; (594 pag.)WO2017/11776; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem