Day: March 18, 2022

Synthetic Route of 169205-95-2, 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.169205-95-2, name is 2-(Methylthio)oxazolo[4,5-b]pyridine, molecular formula is C7H6N2OS, molecular weight is 166.2, as common compound, the synthetic route is as follows.

To a solution of 2-(methylthio)oxazolo[4,5-b]pyri- dine (2.0 g, 12.12 mmol) in THF (5 mL) was added morpholine (5 mL) and heated at 75 C. overnight. The solvent was distilled off to afford the title compound (2.0 g, 83.3%).10210] ?HNMR (DMSO-d5, 300 MHz): oe 8.20-8.10 (d,1H), 7.80-7.70 (d, 1H), 7.15-7.00 (m, 1H), 3.75-3.72 (m,4H), 3.63-3.52 (m, 4H). LCMS: mlz: 206.5 (M+1)+

The chemical industry reduces the impact on the environment during synthesis 169205-95-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; Gummadi, Venkateshwar Rao; Samajdar, Susanta; (82 pag.)US2016/340366; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 851484-95-2, 2-Chloro-5-fluoronicotinaldehyde, 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, 851484-95-2, blongs to pyridine-derivatives compound. Safety of 2-Chloro-5-fluoronicotinaldehyde

2-chloro-5-fluoro-pyridine-3-carbaldehyde (1.00 g, 6 · 27 mmol) was added to a 20 ml microwave vial, 2-benzyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 equivalents, 6.89 mmol) [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride (PdCl2 (dppf); 0 ? 1 equivalent, 0.63 mmol ) And powdered sodium carbonate (3 equiv., 18.8 mmol). Add 1,4-dioxane (9 mL) and water (5 mL) The mixture was rinsed with nitrogen and then passed through a microwave 90 C under heating for two 2 hours. The cooled mixture was then directly adsorbed onto silica and purified by trituration on a 40 g silica gel column eluting with isohexane: ethyl acetate (100%: 0% to 70%: 30%) to afford the title compound as a colorless oil 2-benzyl-5-fluoro-pyridine-3-carbaldehyde (460 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,851484-95-2, its application will become more common.

Reference:
Patent; Xian Zheng Da Cangu Co., Ltd.; G ·mixieer; G ·muensi; N ·P·maerhuolande; M ·C·pulaien; (42 pag.)CN106715425; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 6318-51-0, 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. 6318-51-0, name is (4-Chlorophenyl)(pyridin-2-yl)methanone, molecular formula is C12H8ClNO, 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.

In a 5L autoclave, under the condition of argon, 400 g of (4-chlorophenyl)(pyridin-2-yl)methanone was added from the feed inlet; 3 L of toluene was added; Bubble out of gas, continuous bubbling 30min; degassing is complete. Under an argon atmosphere, 100 mg of catalyst (R,R)-DIOPRuCl2(R)-Me-BIMAH was added from the feed port, and finally 6 g of potassium tert-butoxide was added; after the addition was completed, the feed port was quickly closed tightly. Replacing argon with hydrogen gas and slowly introducing hydrogen gas to 35 atm, and then closing the inflation valve and closing the hydrogen channel; finally stirring, maintaining the reaction at 35 C.; after the start of stirring, the pressure dropped. Observe the changes in pressure, after 4h, the pressure no longer changes, sampling for GC analysis,The conversion rate was 99.7% and the ee value was 98.2%.

According to the analysis of related databases, 6318-51-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Zhongshanyi Antai Pharmaceutical Technology Co., Ltd.; Xu Liang; Mao Bo; Li Yanxiong; (7 pag.)CN107827812; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1003711-43-0, 2-Bromo-5-hydroxy-3-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, Computed Properties of C6H6BrNO, blongs to pyridine-derivatives compound. Computed Properties of C6H6BrNO

To a solution of 487 6-bromo-5-methylpyridin-3-ol (500 mg, 2.66 mmol), 83 bromocyclopropane (1287 mg, 10.64 mmol) and 488 potassium iodide (50 mg, 0.301 mmol) in 106 DMF (4.0 mL) was added 459 cesium carbonate (1300 mg, 3.99 mmol) at RT. The reaction vessel was sealed and heated in a microwave at 150 C. under nitrogen for 1 h. The reaction mixture was cooled to RT and poured into water (20.0 mL) and extracted with ethyl acetate (10.0 mL×3). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash silica gel chromatography to afford the 489 title compound as an oil. MS (ESI) m/z: 229.9[M+H+].

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1003711-43-0, 2-Bromo-5-hydroxy-3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Merck Sharp & Dohme Corp.; Han, Yongxin; Achab, Abdelghani; Deng, Yongqi; Fradera, Xavier; Gibeau, Craig; Hopkins, Brett A.; Li, Derun; Liu, Kun; McGowan, Meredeth A.; Sciammetta, Nunzio; Sloman, David; White, Catherine; Zhang, Hongjun; Zhou, Hua; US2019/144433; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 936011-17-5 ,Some common heterocyclic compound, 936011-17-5, molecular formula is C7H6BrNO2, 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 stirred solution of 5-bromo-2-methoxyisonicotinaldehyde (1.45 g, 6.71 mmol) in nPrOH (60 mL) were added potassium vinyltrifluoroborate (0.899 g, 6.71 mmol), PdCl2(dppf) (98 mg, 0.134 mmol), and TEA (0.94 mL, 6.71 mmol). The reaction mixture was heated to reflux for 3 h, cooled to room temperature, diluted with EtOAc, and washed with water and brine. The organic layer was dried (Na2SO4), concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CDCl3) 6 10.08 (s, IH); 7.90 (d, IH); 7.70 (dd, IH); 6.93 (d, IH); 5.72 (d, IH); 5.43 (d, IH); 4.03 (s, 3H).

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. 936011-17-5, 5-Bromo-2-methoxyisonicotinaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/50383; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1147422-00-1, 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. 1147422-00-1, name is tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate. A new synthetic method of this compound is introduced below.

5-(2-amino-4-(4-chlorothiophen-2-yl)thiazol-5-yl)-octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate tert-butyl octahydro-1H-pyrrolo[3,2-c]pyridin-1-carboxylate (100mg, 0.4mmol), and 5-bromo-4-(4-chloro-thiophen-2-yl)-thiazole-2-amine (157mg, 0.5mmol) were added to N,N-dimethylformamide (4mL), and then triethylamine (447mg, 4.4mmol) was added. The mixture was warmed to 90C and reacted for 6 h. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic phases were combined and washed successively with water and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated to produce a crude product. The crude product was purified with a silica gel column chromatography to produce the title compound as a yellow solid (170mg). ESI-MS (m/z): 441.2 [M + H]+

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1147422-00-1, tert-Butyl octahydro-1H-pyrrolo[3,2-c]pyridine-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Sichuan Kelun-Biotech Biopharmaceutical Co., Ltd.; CAI, Jiaqiang; YU, Nan; ZENG, Hong; SONG, Hongmei; QING, Yan; SONG, Shuai; DENG, Hanwen; TANG, Zujian; DUAN, Xiaofan; HUANG, Haitao; YE, Hong; LIU, Gang; WANG, Lichun; WANG, Jingyi; (81 pag.)EP3511332; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 133081-25-1 ,Some common heterocyclic compound, 133081-25-1, molecular formula is C11H15N3O4, 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.

A mixture of 2-chloro-4,6-dimethyl-1,3,5-triazine (CDMT) (1.76 g, 10 mmol), 2 (2.53 g, 10 mmol) in THF (10 ml), and N-methylmorpholine (1.1 ml, 10 mmol) and after 4 h 4b (2.83 g, 10 mmol) in THF were combined as above to afford 5b as yellow solid. Compound 5b: mp 188-190 C; yield 38%; IR (KBr) nu (cm-1): 1522.0, 1636.2, 1717.8, 2862.6, 2934.4, 3242.6; 1H NMR (CD3OD) (delta ppm): 8.4 (2H, d, J = 8.1 Hz, ArH), 7.7-7.9 (2H, m, ArH), 7.6 (1H, d, J = 5.8 Hz, CCHC), 7.5 (1H, t, J = 5.7 Hz, ArH), 6.6 (1H, d, J = 8.7 Hz, CCHC), 4.6 (2H, s, NH), 3.9-4.0 (2H, m, NHCH2), 3.7 (1H, m, NH), 3.3-3.4 (2H, m, CH2N), 3.0 (2H, m, CH2), 2.7 (2H, m, CH2), 2.5 (1H, m, NH), 1.8-2.0 (8H, m, CH2), 1.7 (2H, m, CH2), 1.4-1.5 (9H, m, BOC); MS (FAB) m/z (M + 1) 519.4, 419.3, 199.1; MS-HR (FAB) Calcd for C28H38N6O3: 518.30054. Found: 519.30688 (M + 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,133081-25-1, its application will become more common.

Reference:
Article; Szymanski, Pawel; Markowicz, Magdalena; Mikiciuk-Olasik, Elbieta; Bioorganic Chemistry; vol. 39; 4; (2011); p. 138 – 142;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 73112-16-0, 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. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine, molecular formula is C6H5Br2N, 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.

2,6-Dibromo-4-methylpyridine (3.76 g, 14.98 mmol) in dichloromethane (DCM) (80 mL) was added.Cool to -78 C. under nitrogen.While maintaining the internal temperature below -70 C,n-Butyllithium (2.5 M in hexane) (6.59 mL, 16.48 mmol) was added dropwise.After the addition is completeThe solution becomes a suspensionStir at -78 C. for 15 minutes.While keeping the internal temperature below -60 C,A solution of dihydrofuran-3 (2H) -one (1.548 g, 17.98 mmol) in 2 mL of DCM was added over 3 minutes.After the addition is completeReduce the temperature back to -78 C,Stir for 30 minutes.The product with saturated aqueous NH4Cl,Extracted with DCM.The organic portion was dried over MgSO 4, filtered and concentrated to give a residue that was purified on a silica gel column eluted with 0-50% ethyl acetate / heptane to give the product (2.13 g, yield). 55%).

According to the analysis of related databases, 73112-16-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Abbvie Incorporated; Argiriadi, Maria A.; Breinlinger, Eric C.; Chien, Ellen Yulin Tsai; Cowart, Marlon D.; Frank, Kristine E.; Friedman, Michael M.; Hardy, David J.; Herold, J. Martin; Liu, Huaqing; Chu, Wei; Scanio, Marc J.; Schrimpf, Michael R.; Vargo, Thomas R.; Van Epps, Stacy A.; Webster, Matthew P.; Little, Andrew J.; Dunstan, Teresa A.; Katcher, Matthew H.; Schedler, David A.; (232 pag.)JP6557436; (2019); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1026796-81-5 , The common heterocyclic compound, 1026796-81-5, name is N-(4-Bromopyridin-2-yl)acetamide, molecular formula is C7H7BrN2O, 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.

Step 2: N-[4-(trimethylstannyl)pyridin-2-yl]acetamide Intermediate 20 A mixture of N-(4-bromopyridin-2-yl)acetamide (12.6 g, 58.7 mmol), hexamethylditin (25 g, 76.3 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.39 g, 2.93 mmol) in 1,4-dioxane (300 mL) was heated at 95 C. for 3 h. The solvents were removed under reduced pressure. DCM was added and the resulting black precipitate was removed by filtration and washed with DCM. The filtrate was evaporated. The residue was purified by silica gel chromatography (25-40% EtOAc/hexanes) to afford N-[4-(trimethylstannyl)pyridin-2-yl]acetamide (12.6 g, 72%). 1H NMR (400 MHz, CDCl3) delta ppm 8.33 (s, 1H), 8.22 (s, 1H), 8.17 (dd, J=4.7, 0.9 Hz, 1H), 7.14 (dd, J=4.7, 0.6 Hz, 1H), 2.20 (s, 3H), 0.34 (s, 9H).

The synthetic route of 1026796-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmacuticals, Inc.; US2012/15943; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 75291-85-9 ,Some common heterocyclic compound, 75291-85-9, molecular formula is C6H4BrClN2O, 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.

Preparation 119tert-butyl (3R,4S)-4-[(5-bromo-3-carbamoylpyridin-2-yl)oxyl-3-fluoropiperidine- 1 -carboxylate A solution of 5-bromo-2-chloronicotinamide (Preparation 177, 11.7 g, 49.8 mmol), tert-butyl (3R,4S)-3-fluoro-4-hydroxypiperidine-1 -carboxylate (WO 20131011402 Al, 10.9 g, 49.8 mmol) and potassium tert-butoxide (6.72 g, 60 mmol) in DMSO (165 mL) was stirred at roomtemperature for 16 hours. The reaction was quenched by the addition of water (500 mL) and extracted into EtOAc (3 x 500 mL). The organic layers were combined, concentrated in vacuo and the residue triturated with diethylether to afford the title compound as a pale yellow powder(17.8 g, 85%).1H NMR (400 MHz, DMSO-d6): O ppm 1.39 (5, 9H), 1.82 (m, 1H), 1.94 (m, 1H), 3.01 (m, 1H),3.27 (m, 1H), 3.93 (5, 1H), 4.14 (5, 1H), 4.98 (d, 1H), 5.38 (dddd, 1H), 7.51 (5, 1H), 7.90 (5, 1H),8.26 (d, 1H), 8.41 (d, 1H). MS mlz 418 [M79Br-fH]

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. 75291-85-9, 5-Bromo-2-chloronicotinamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; SKERRATT, Sarah Elizabeth; BAGAL, Sharanjeet Kaur; SWAIN, Nigel Alan; OMOTO, Kiyoyuki; ANDREWS, Mark David; WO2015/92610; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem