Category: pyridine-derivatives

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

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 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: 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 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

Application of 766557-60-2, Adding some certain compound to certain chemical reactions, such as: 766557-60-2, name is 2-Ethoxy-3-iodopyridine,molecular formula is C7H8INO, 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 766557-60-2.

EXAMPLE 1 N-fi-Cyano-i-fP^-dimethoxyphenyQsulphonyll-S-p-ethoxypyridin-S-yO^-oxo^S- dihydro- 1 H-indol-3-yl]-4-(1 -methylpiperidin-4-yl)piperazine- 1 -carboxamide; 1 a) 3-(2-Ethoxypyridin-3-yl)-3-hydroxy-5-iodo- 1, 3-dihydro-2H-indol-2-oneWith ice-bath cooling, 20.86 g (76.40 mmol) of 5-iodoisatin were stirred in 400 ml of anhydrous tetrahydrofuran (THF), and 3.22 g (80.50 mmol, 60% w/w) of sodium hydride were added a little at a time, the temperature being kept between 0-100C. With ice-bath cooling, the suspension was stirred for one hour, during which the pyridine Grignard reagent was prepared. At room temperature, 20 g (80.30 mmol) of the 2-ethoxy-3- iodopyridine were dissolved in 400 ml of anhydrous THF, and over a period of 5-10 minutes 95.6 ml (1 M solution in THF, 95.60 mmol) of ethylmagnesium bromide were added to this solution with cooling, at a temperature between 22 and 15C. The solution was stirred for 20 minutes, during which time the colour changed from colourless to slightly yellowish. The solution of the pyridine Grignard reagents was then, over a period of 5-10 minutes, added to the solution, cooled in an ice-bath, of the 5-iodoisatin sodium salt, the temperature fluctuating between 5 and 18C. After the addition of the Grignard reagent had ended, the ice-bath was removed, and the reaction mixture was stirred at room temperature for another 2 hours. Excess saturated ammonium chloride solution was added, followed by ethyl acetate, and the mixture was stirred for another 5 minutes. The aqueous phase was removed and extracted with ethyl acetate (2 x). The combined organic phases were washed with water (2 x), and the solvent was removed under reduced pressure. Initially, unreacted 5-iodoisatin precipitated from the still dilute solution and was removed, and after further concentration the product, too, crystallized out. The suspension was stored in a refrigerator at 5C for two hours and the slightly yellowish solid was then filtered off and washed with a little ethyl acetate. The desired 3-(2- ethoxypyridin-3-yl)-3-hydroxy-5-iodo-1 ,3-dihydro-2/-/-indol-2-one (17.1 g, 43.16 mmol, 57%) was isolated after drying at 400C.ESI-MS [M+H+] = 397.05 Calculated for Ci5H13IN2O3 = 396.19

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. 766557-60-2, 2-Ethoxy-3-iodopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/80970; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 117873-72-0, 2,6-Dibromo-4-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, name: 2,6-Dibromo-4-methoxypyridine, blongs to pyridine-derivatives compound. name: 2,6-Dibromo-4-methoxypyridine

A solution of 2.00 g 2,6-dibromo-4-methoxy-pyridine in 80 g liquid ammonia under was heated in an autoclave to 140 C. for 4 h. The reaction was cooled to room, evaporated and the residue was purified by silica column chromatography to yield 0.457 g of the title compound as white solid. MS (ISP) M+H+=203.2 205.5; 118b) 6-Bromo-4-methoxy-pyridin-2-ylamineA solution of 2.00 g 2,6-dibromo-4-methoxy-pyridine in 80 g liquid ammonia under was heated in an autoclave to 140 C. for 4 h. The reaction was cooled to room, evaporated and the residue was purified by silica column chromatography to yield 0.457 g of the title compound as white solid. MS (ISP) M+H+=203.2 205.5

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117873-72-0, 2,6-Dibromo-4-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Haap, Wolfgang; Hebeisen, Paul; Kitas, Eric A.; Kuhn, Bernd; Mohr, Peter; Wessel, Hans Peter; US2009/143439; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 86847-84-9 ,Some common heterocyclic compound, 86847-84-9, molecular formula is C10H13ClN2O, 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 dry solution OF N- (6-CHLOROPYRIDIN-2-YL)-2, 2-dimethyl propionamide (Preparation 107, 8. 0g, 37. 6MMOL) in THF (120ML), cooled TO-78C, was added dropwise, a solution of tert-butyllithium in pentane (1.7M, 48.7mL, 82. 8MMOL) over 40min. The reaction was stirred at-78C for 3h before adding a solution of iodine (11. 46g, 45. 1MMOL) in THF (40mL) dropwise. The mixture was brought up to rt and stirred for 16h. 2M HCl (30mL) was added to the reaction, and after 20min the solvent was removed in VACUO. Crude material was partitioned between ethyl acetate (200ML) and water (150ML). Organics were separated and washed with 10% sodium thiosulfate solution (4XLOOML) then NAHCO3 solution (2XLOOML), dried (MGS04) and the solvent removed in VACUO. The residue was purified by column chromatography (SIO2, CH2C12) to give the title compound. m/z (ES) = 338.93 [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. 86847-84-9, N-(6-Chloropyridin-2-yl)pivalamide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
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. 195044-14-5, name is 2-Bromo-6-tert-butylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Bromo-6-tert-butylpyridine

To a 250 mL three-necked flask was added 3-methoxyphenylboronic acid (3.1 g, 20.0 mmol) K2CO3 (5.8 g, 42.0 mmol), and then a reflux device was set up, and the gas was purged three times in an argon atmosphere. 2-Bromo-6-tert-butylpyridine (3.6 g, 16.8 mmol), solvent ethylene glycol dimethyl ether (30 mL) and distilled water (20 mL) were added. The system was then bubbled with a long needle for 30 min and then tetrakistriphenylphosphine palladium (1.0 g, 0.9 mmol) was added. The system was heated to reflux for 12 h under argon. After the reaction was completed, the system was cooled to room temperature, and ethyl acetate (30 mL EtOAc) was evaporated. 1:100), 2.7 g of colorless oil2-(3-Methoxyphenyl)-6-tert-butylpyridine, yield 67%.

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, 195044-14-5, 2-Bromo-6-tert-butylpyridine.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Organic Chemistry Institute; Huang Zheng; Jia Xiangqing; Guo Le; (26 pag.)CN104804041; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 75806-86-9, Adding some certain compound to certain chemical reactions, such as: 75806-86-9, name is 2-Bromo-5-chloro-3-nitropyridine,molecular formula is C5H2BrClN2O2, 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 75806-86-9.

Example 121 : 5-Chloro-3-(4-chloro-3- (trifluoromethyl)phenylsulfonamido)picolinic acid; [00525] Step 1 : A dry 250 mL flask was charged with 2-bromo-5-chloro-3- nitropyridine (24 g, 10 mmol), CuCN (19 g, 20 mmol) and DMF (100 mL). The resultant mixture was stirred at 110 C for 2 h and then concentrated under reduced pressure. Water (100 mL) was added and the aqueous layer was extracted with EtOAc (250 mL X 3). The combined organic layer was washed with brine, dried (MgSO4), and evaporated in vacuo to afford a light yellow solid (15 g) which was used directly for the next step.

According to the analysis of related databases, 75806-86-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; WO2006/76644; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem