Category: pyridine-derivatives

Application of 1042141-37-6, 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 1042141-37-6, name is Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-bromoimidazo[1,2-ajpyridine-6-carboxylate (300 mg, 1.18 mmol) dissolved in diethyl ether (12 mL) and cooled to 0 C was treated with lithium aluminum hydride (46 mg, 1.21 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. Aftercooling to 0 C again, the reaction mixture was quenched by addition of sodium sulfate decahydrate. The mixture was stirred for 20 mm and filtered. The filtrate was concentrated to give (2-bromoimidazo[1,2- ajpyridin-6-yl)methanol.

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 1042141-37-6, Methyl 2-bromoimidazo[1,2-a]pyridine-6-carboxylate.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; APPLEBY, Todd; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; GUERRERO, Juan A.; JABRI, Salman Y.; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; NOTTE, Gregory; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; VENKATARAMANI, Chandrasekar; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (724 pag.)WO2018/195321; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 15862-50-7, 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 15862-50-7 as follows.

Dioxane (10.4 L, 8 v), 1 (1.3 kg, 1.0 eq.), KOAc (1.65 kg, 3.0 eq.), and B2Pin2 (1.7 kg, 1.2 eq.) were charged into 20 L reactor. Nitrogen was bubbled into the solution to remove any excess oxygen for 1 hour at 20~30C. Pd(dppf)Cl2 (125.6 g, 0.03 eq.) was into the reactor into the mixture under nitrogen. The mixture was heated to 80~90C. Thehe reaction mixture stirred for 3 hours at until HPLC showed the reaction was completed. The reaction mixtiire was cooled to 20-30C and then filtered. The filtered cake was washed with dioxane (2.6 L, 2 v). The filtered solutions were combined and concentrated and then transferred to 20 L reactor. H2O2 (3.25 L, 2.5 v) was added at 20~50C, and the temperature was increased from 23 to 50C. The reaction misture was stirred for 30-60 min until HPLC showed the reaction was completed. H2O (6.5 L, 5 v) was added in to the mixture, and the mixture was extracted with DCM (13.0 L, 10 v) twice. The organic phase was collected and washed with 15% brine (6.5 L, 5 v) twice, and was then extracted with 15% Na2C03 (6.5 L, 5 L) twice. The aqueous phase was colleted and the pH value was ajdjusted 10-1 1 to 4-5 with 3M HC1. The aqueous phase was then extracted with EA (13.0 L, 10.0 v) twice. The organic phase was collected and concentrated to about dryness, and heptane (6.5 L, 5.0 v) was added to slurry for 1 hour at 20~30C. The slurry was filtered, and the filtered cake was washed with heptane (650 ml, 0.5 v), drid in oven at 30~40C for overnight to obtain 650.2 g product as brown solid with purity: 99.6%, yield: 67.8%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,15862-50-7, its application will become more common.

Reference:
Patent; EPIZYME, INC.; CAMPBELL, John Emmerson; DUNCAN, Kenneth William; MILLS, James Edward John; MUNCHHOF, Michael John; (301 pag.)WO2019/79540; (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

Related Products of 84539-34-4, 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.84539-34-4, name is 4-Amino-3,5-dibromopyridine, molecular formula is C5H4Br2N2, molecular weight is 251.91, as common compound, the synthetic route is as follows.

(2) diazotization reaction:A 200 ml three-necked flask was charged with 0.045 mol of concentrated sulfuric acid having a concentration of 17.5 mol / L and 2.52 g (0.01 mol)3,5-dibromo-4-aminopyridine,After 3,5-dibromo-4-aminopyridine is completely dissolved,1.78g (0.014mol) nitrosylsulfuric acid was added dropwise at 52 C, the end of the reaction was tested by using potassium iodide starch test paper. When the reaction solution turned the potassium iodide starch test paper blue and did not fade, the reaction was stopped for 1.2h,To give 3,5-dibromo-4-pyridin-sulfonic acid

Statistics shows that 84539-34-4 is playing an increasingly important role. we look forward to future research findings about 4-Amino-3,5-dibromopyridine.

Reference:
Patent; Shanghai Wohua Chemical Co., Ltd.; Hu Yadong; Yang Benmei; (5 pag.)CN106957259; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1186194-46-6, 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 1186194-46-6, name is 5-Bromo-6-methoxynicotinic acid. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: 1 -{[5-Bromo-6-methoxy-pyridine-3-carbonyl]-amino}-cycloheptanecarboxylic acid methyl esterThe compound of step 1 (1 .85 g, 7.97 mmol) was dissolved in thionyl chloride (6 ml) and stirred for 30 min at 60 C. The volatiles were evaporated in vacuo, the residue was dissolved in DCM and added to a stirred mixture of 1 -amino- cycloheptanecarboxylic acid methyl ester hydrochloride, EA and saturated sodium hydrogencarbonate solution with ice cooling. The mixture was stirred at room temperature overnight, the phases were separated and the aqueous phase was extracted with EA. The combined organic phases were dried over sodium sulfate and evaporated to dryness to yield the title compound (2.80 g).1H-NMR: delta = 8.62 (d, 1 H); 8.52 (s, 1 H); 8.48 (d, 1 H); 3.99 (s, 3H); 3.57 (s, 3H); 2.15- 2.01 (m, 4H); 1 .65-1 .43 (m, 8H)

According to the analysis of related databases, 1186194-46-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; PERNERSTORFER, Josef; KLEEMANN, Heinz-Werner; SCHAEFER, Matthias; SAFAROVA, Alena; PATEK, Marcel; WO2011/53948; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem