Tag: M.W:100-200

Application of 52605-96-6 ,Some common heterocyclic compound, 52605-96-6, molecular formula is C6H6ClNO, 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.

2, 3-Dimethoxypyridine (40) To a stirring solution of sodium methoxide (300.0 mL, 30% in methanol) was added 2-chloro-3-methoxypyridine (55.0 g, 383.1 mmol). The reaction mixture was stirred at 80 C. overnight. After the reaction was completed, the mixture was evaporated in vacuo. The residue was dissolved with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo. The residue was purified by flash chromatogram with ethyl acetate/petroleum ether (1:5) to afford 2,3-dimethoxypyridine (40) as yellow oil (42.0 g, 79%). ESI-MS, m/z=140 [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. 52605-96-6, 2-Chloro-3-methoxypyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsai, Guochuan Emil; Wang, Ching-Cheng; Hsieh, Yuan-Ting; (53 pag.)US2019/112289; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 33252-29-8 ,Some common heterocyclic compound, 33252-29-8, molecular formula is C6H3ClN2, 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.

General procedure: In a 1L four-necked flask equipped with a mechanical stirring and condensation device,Put in homemade 2-chloro 6-cyanopyridine (calculated as pure product,The same below) 600g, tungsten hexachloride 12g, phosphorus pentachloride 12g, atmospheric pressure,Heat up to 150 , start stirring, and continuously introduce chlorine gas at a rate of 100mL/min.Control the reaction temperature at 150 ~ 155 , continuous reaction for 20h,Sampling gas chromatography analysis, raw material conversion rate and product yield are shown in Table 2.

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. 33252-29-8, 6-Chloropicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Hong Sun Biochemical Co., Ltd.; Chen Honglong; Mu Dengyou; Wang Fujun; Jiang Jianhua; Xue Yi; Chen Xinchun; (7 pag.)CN111072558; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 160590-36-3, 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. 160590-36-3, name is 2-Methoxy-3-nitro-4-methylpyridine. A new synthetic method of this compound is introduced below.

Sodium acetate (365 g, 5.37 mol) was added to a stirred solution of 2-methoxy-4-methyl-3-nitropyridine (250 g, 1.49 mol) in acetic acid (1 .5 L) at ambient temperature and then Br2(639 g, 4.00 mol) was added dropwise (30 mm). After addition, the mixture was heated at 80C for 12 h, at which time TLC indicated the reaction had gone to completion. The mixturewas cooled (0 C) and quenched by sequential addition of 10% aqueous (1.5 L) and saturatedaqueous sodium sulfate (1.5 L). The resulting solid was collected by filtration, washed withwater, and dried under reduced pressure to give the title compound (302 g, 82.2% yield) as alight yellow solid. h11 NMR (400 MHz, DMSO-d6): 6 8.25 (s, 1 H), 3.94 (s, 3 H), 2.29 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,160590-36-3, 2-Methoxy-3-nitro-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HEWITT, Michael, Charles; HSIAO-WEI TSUI, Vickie; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F., Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (197 pag.)WO2016/77378; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1137-67-3, 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. 1137-67-3, name is 2-(Pyridin-3-yl)-1H-benzo[d]imidazole, molecular formula is C12H9N3, 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: A solution of 2-(3-pyridyl)-1H-benzimidazole, L1, (0.34 g,1.79 mmol) in methanol (4 ml) was added to a solution ofZn(OAc)22H2O (0.39 g, 1.79 mmol) in methanol (6 ml).The mixture was stirred for 24 h at room temperature to give a white precipitate. After the reaction period, the precipitate was filtered off, washed with methanol (3 9 20 mL) and dried to afford complex 1 as a white 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 1137-67-3, 2-(Pyridin-3-yl)-1H-benzo[d]imidazole.

Reference:
Article; Zaca, Thembisile P.; Ojwach, Stephen O.; Akerman, Matthew P.; Transition Metal Chemistry; vol. 41; 6; (2016); p. 663 – 673;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 112110-07-3, 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. 112110-07-3, name is 5-(Trifluoromethyl)pyridin-3-amine, molecular formula is C6H5F3N2, 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.

Under a nitrogen atmosphere, 0.1 g (0.25 mmol, 1.0 eq) of JD1001-002-12 was sequentially added to a 25 mL reactor.3.2 mL (10.0 V) THF, 0.32 g (0.75 mmol, 3.1 eq) NaHCO3, 0.38 g (0.75 mmol, 3.0 eq) 2-amino-5-trifluoromethylpyridine, heated to 60 C, stirred for 3 hours, TLC The reaction of the raw materials is detected (developing agent: PE/EA=1/1,UV254), the reaction was stopped, the reaction was quenched with water and extracted with ethyl acetate. Filtration and concentration of the organic phase gave a solid, which was purified by HPLC (CH3CN/H2O = 60:40) to afford 39 mg of JD1001-2111. Yield31%.

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 112110-07-3, 5-(Trifluoromethyl)pyridin-3-amine.

Reference:
Patent; Kunming Jida Pharmaceutical Co., Ltd.; Xiao Xuzhi; Zhang Poyong; Lu Faguan; Wang Zhipeng; Chen Mengran; Guo Kun; Zhou Rui; Zhang Yun; (28 pag.)CN109593061; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 83393-46-8, 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. 83393-46-8, name is 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)ethanone, molecular formula is C9H8N2O, 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.

(E)-3-chloro-3-(lH-pyrrolo[2,3-b]pyridin-3-yl)acrylaldehyde:; Phosphorous oxychloride (3.7 mL, 40 mmol) was added dropwise to DMF (6.2 mL, 80 mmol) at 0 C. The reaction mixture was let warm to room temperature and stirred for 15 minutes. 1-(lH-Pyffolo[2,3-b]pyridin-3-yl)-ethanone was added in DMF (20 mL) and the reaction heated to 60 C for 4 hours, cooled to 0 C and 150 mL of saturated NaOAc solution added. The reaction mixture was heated briefly to 50 C and then extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to an oil which contains impure product. Upon standing a solid precipitated from the aqueous layer to give 0.9 g of a brown solid, 4.3 mmol, 22% yield.

According to the analysis of related databases, 83393-46-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2005/103050; (2005); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 18699-87-1, 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 18699-87-1, name is 2-Methyl-3-nitropyridine. This compound has unique chemical properties. The synthetic route is as follows.

Add tetrahydrofuran (2.7 L) to a 22-L, 3-neck flask fitted with a stirrer, temperature probe and an addition funnel fitted with a gas inlet adapter for N2, and cool to about 2 C. Add sodium ethoxide (0.409 kg, 6.02 mol, 2.0 equiv.) in one portion. One observes a slight exotherm to 2.7 C. Stir the mixture for 20 min, add diethyl oxalate (1.22 L, 9.03 mol, 3.0 equiv.) at -0.34 C. over 50 min (slightly exothermic) and then stir the mixture for 10 min. Add a solution of 2-methyl-3-nitropyridine (2a-1, 0.415 kg, 3.01 mol, 1.0 equiv.) and THF (0.625 L) at 4-9 C. over 22 min without cooling. Allow the mixture to warm to rt over 1 h. Monitor progress of the reaction by HPLC (Agilent series 1100 using the following conditions: Waters Symmetry C8 (5mu) column (3.9×150 mm), flow rate at 1.0 mL/min; CH3CN/0.1% aq. TFA, 55/45; lambda=210 nm; RT: 2-methyl-3-nitropyridine 2a-1=1.8 min, 3a-1=2.7 min). Typically one observes >99% conversion to product within 2-3 h. During the reaction, a thick red precipitate forms. Cool the reaction mixture to about 1 C. and add saturated NH4Cl solution (2.0 L) at 1 C. to 9 C. Add water (5.9 L) (pH 7.4) and then add IPA (3.5 L). Stir the mixture for 1 h and collect the red colored solid by filtration. Wash the filter cake with IPA/H2O (1:4, 8.0 L), H2O (15 L) and air dry. Dry the filter cake (40 C./0.1 in Hg) to give 3a-1 (0.635 kg, 89%). 1H NMR (CDCl3) delta 1.40 (t, 3H, J=7 Hz), 4.38 (q, 2H, J=7 Hz), 7.36 (m, 2H), 8.42 (dd, 1H J=1.5, 8.4 Hz), 8.66 (dd, 1H, J=1.5, 4.8 Hz), 14.52 (2, 1H, OH).

According to the analysis of related databases, 18699-87-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US2005/131012; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 72093-03-9, name is 3-Chloro-2-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Product Details of 72093-03-9

Preparation of teit-butyl 4-((3-chloropyridin-2-yl)methyl)-4- hydroxypiperidine-l-carboxylate. A solution of 3-chloro-2-methylpyridine (64.2 mg, 0.50 mmol) in THF (1 mL) was sparged with N2 and cooled to -78 C before n-butyllithium (2.5 M THF, 0.16 mL, 0.41 mmol) was added dropwise. After stirred at -78 C for 45 min, the mixture was warmed to RT and stirred for 2 h before cooled again to -78 C. A solution of tert-butyl 4-oxopiperidine-l-carboxylate (74.2 mg, 0.37 mmol) in THF (1.5 mL) was added dropwise. After stirring for 2 hr at -78 C, the mixture was warmed to rt and stirred for 2 d. The reaction was then partitioned between EtOAc and sat. H4CI (aq). After phase-separation, the aqueous was extracted with EtOAc (3x). The organic extracts were combined, dried over Na2S04, filtered and concentrated. The residue was purified by silica chromatography (10-90% EtOAc in hexanes) to afford the title compound as a colorless oil (103.5 mg, 85%). MS (apci) m/z = 227.1 (M+H-Boc).

With the rapid development of chemical substances, we look forward to future research findings about 72093-03-9.

Reference:
Patent; ANDREWS, Steven W.; ARONOW, Sean; BLAKE, James F.; BRANDHUBER, Barbara J.; COLLIER, James; COOK, Adam; HAAS, Julia; JIANG, Yutong; KOLAKOWSKI, Gabrielle R.; MCFADDIN, Elizabeth A.; MCKENNEY, Megan L.; MCNULTY, Oren T.; METCALF, Andrew T.; MORENO, David A.; RAMANN, Ginelle A.; TANG, Tony P.; REN, Li; WALLS, Shane M.; (946 pag.)WO2018/71454; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 156072-84-3, 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 156072-84-3 as follows.

[0307] Cesium carbonate (0.734 g, 2.25 mmol) and 5-chloro-3-methylpyridine-2-carbonitrile (0.206 g, 1.35 mmol) wereadded at room temperature to a suspension of the optically active form of cis-1-(diphenylmethyl)-5-hydroxy-3-(piperidin-4-yl)-4-(trifluoromethyl)-1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridin-6-one (0.212 g, 0.451 mmol) produced in ReferenceExample 27 in DMSO (2 mL), and the mixture was stirred at 150C for 2 hours. The reaction suspension wascooled to room temperature, then diluted with ethyl acetate, and washed with brine. The obtained organic layer wasdried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residuewas purified by silica gel column chromatography [elute: hexane/ethyl acetate = 92/8 – 50/50 (gradient)] to obtain thetitle compound (0.226 g, yield: 86%, optically active form).[0308] 1H-NMR (400MHz, CDCl3) delta: 8.14 (1H, d, J=3Hz), 7.40-7.36 (6H, m), 7.12-7.06 (5H, m), 6.91 (1H, d, J=3Hz),6.69 (1H, s), 4.53 (1H, d, J=7Hz), 3.94-3.86 (3H, m), 3.69 (1H, d, J=3Hz), 3.08-3.00 (2H, m), 2.89-2.81 (1H, m), 2.45(3H, s), 2.02-1.80 (4H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,156072-84-3, its application will become more common.

Reference:
Patent; Daiichi Sankyo Company, Limited; KOBAYASHI, Hideki; ARAI, Masami; KANEKO, Toshio; TERASAKA, Naoki; (95 pag.)EP3081566; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 50501-38-7, Adding some certain compound to certain chemical reactions, such as: 50501-38-7, name is 6-(Hydroxymethyl)picolinonitrile,molecular formula is C7H6N2O, 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 50501-38-7.

P4: For alternative syntheses, see [36?38]. The reaction was performed under nitrogen. SeO2 (386 mg, 3.48 mmol) and P3 (933 mg, 6.96 mmol) were stirred in dioxane (30 mL; neither dried nor degassed) at 110°C (bath temperature) for 24 h to give a dark yellow solution and black precipitate of selenium. The mixture was filtered through Celite to remove selenium. Celite was washed with CH2Cl2. Purification by chromatography (10 g of silica; CH2Cl2)gave pale yellow eluate of the product. White solid: 692 mg(5.24 mmol; 75percent; C7H4N2O; MW 132.12).

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. 50501-38-7, 6-(Hydroxymethyl)picolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shavaleev, Nail M.; Eliseeva, Svetlana V.; Inorganica Chimica Acta; vol. 427; (2015); p. 81 – 86;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem