Tag: M.W:100-200

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. 63572-73-6, name is 5-Nitro-1H-pyrazolo[3,4-b]pyridine. A new synthetic method of this compound is introduced below., SDS of cas: 63572-73-6

10 % Palladium on carbon (40 mg) was added to a solution of 5-nitro-1H-pyrazolo[3,4-b]pyridine (A) (308 mg, 1.876 mmol) in ethanol and tetrahydrofuran and the mixture was charged with H2 (gas). After stirring the reaction mixture for 15 h, the mixture was filtered using celite and purified by column chromatography. The desired product 1H-pyrazolo[3,4-b]pyridin-5-amine (B) (73 mg) was obtained as 89 % yield.

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, 63572-73-6, 5-Nitro-1H-pyrazolo[3,4-b]pyridine.

Reference:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; WO2013/13816; (2013); 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.156072-84-3, name is 5-Chloro-2-cyano-3-methylpyridine, molecular formula is C7H5ClN2, molecular weight is 152.58, as common compound, the synthetic route is as follows.COA of Formula: C7H5ClN2

A mixture of 2-bromo-5-chloro-3-methylpyridine (45 g, 218 mmol), zinc cyanide (8.30 mL, 131 mmol), tris(dibenzylideneacetone) dipalladium (0) (4.99 g, 5.45 mmol), and 1 ,1?-bis(diphenylphosphino)ferrocene (6.04 g, 10.90 mmol) in dimethylacetamide (40 mL) was heated to 110 C for 4 h. The reaction mixture was cooled to RT, diluted with water and extracted with EtOAc. The organic phase obtained was concentrated under reduced pressure and residue purified by chromatography on silica gel using ISCO eluting with 0-60% EtOAc/hexanes to afford 5-chloro-3-methylpicolinonitrile (25.4 g, 166 mmol, 76 % yield). LC/MS (ESI+) m/z = 153.1 (M+H) . To a solution of 5-chloro-3-methylpicolinonitrile (24.0 g, 157 mmol) in EtOH (100 mL) was added NaOH (110 mL of 5 N solution, 550 mmol). The resulting mixture was refluxed at 90 C for 18 h. After cooling to RT, the reaction mixture was concentrated. The residue was diluted with water and the pH of the solution was adjusted to 4 by addition of 5 N HCl. The solid that precipitated was filtered and set aside. The filtrate was extracted with EtOAc (2 x). The aqueous layer was again acidified with 5 N HCl to pH 4 and extracted with EtOAc (2 x). The EtOAc extracts were combined, dried, and concentrated. The solid obtained from all the workup steps were combined and dried in a vacuum oven at 40 C for 12 h to give 5-chloro-3-methylpicolinic acid (268) (24.1 g, 140 mmol, 89% yield). LC/MS (ESI+) m/z = 172.0 (M+H) +. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 11.29 (br. s., 1 H), 8.41 (d, J=1.76 Hz, 1 H), 7.73 (d, J=1.76 Hz, 1 H), 2.75 (s, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,156072-84-3, 5-Chloro-2-cyano-3-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; AMEGADZIE, Albert; BOURBEAU, Matthew P.; BROWN, James A.; CHEN, Jian J.; CHENG, Yuan; FROHN, Michael J.; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; LIU, Longbin; LIU, Qingyian; LOW, Jonathan D.; MA, Vu Van; MANNING, James; MINATTI, Ana Elena; NGUYEN, Thomas T.; NISHMURA, Nobuko; NORMAN, Mark H.; PETTUS, Liping H.; PICKRELL, Alexander J.; QIAN, Wenyuan; RUMFELT, Shannon; RZASA, Robert M.; SIEGMUND, Aaron C.; STEC, Markian M.; WHITE, Ryan; XUE, Qiufen; (759 pag.)WO2016/22724; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1403899-44-4, 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. 1403899-44-4, name is 6-Chloro-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine, molecular formula is C9H11ClN2, 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 10: 6-Chloro-3,3-di methyl-2,3-di hydro-pyrrolo[3,2-c] pyridi ne-I -carboxyl ic acid tert-butyl esterTo a solution of 6-chloro-3,3-dimethyl-2,3-dihydro-1 H-pyrrolo[3,2-c]pyridine (1.3 g, 7.4 mmol)in THF (20 mL) were added teit-butyl dicarbonate (4.1 g, 18.6 mmol) and dimethyl-pyridin-4-yl-amine (2.22 g, 18.6 mmol) and the solution was stirred for 2 h. Water (60 mL) was addedand the product was extracted with EtOAc. The organic phase was washed with brine, dried (MgSO4), filtered and evaporated. Chromatography (Si02, eluted with petrol – EtOAc 0-40%) gave the title compound (1.04 g). 1H NMR (Me-d3-OD): 8.04 (1H, 5), 7.60 (1H, 5), 3.81 (2H,5), 1.59 (9H, 5), 1.40 (6H, 5). MS: [M+H] = 283.Alternative procedure: Potassium teit-butoxide (600 mg, 5.36 mmol) was added to a stirred solution of 6-chloro-3,3-dimethyl-2,3-dihydro-1 H-pyrrolo[3,2-c]pyridine (800 mg, 4.38 mmol) in anhydrous THF (15 mL) and the mixture was stirred at room temperature for 10 minutes. Asolution of di-teit-butyl dicarbonate (1.07 g, 4.89 mmol) in anhydrous THF (15 mL)was added and the mixture was stirred at room temperature overnight. The organic solvent was removed in vacuo, the aqueous residues were diluted with water (100 mL) and extracted with EtOAc (2 x 200 mL). The organic layers were combined and the solvent was removed in vacuo to afford the title compound (1.19g, 96%), NMR data consistent with those previouslyobtained.

According to the analysis of related databases, 1403899-44-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; CHESSARI, Gianni; JOHNSON, Christopher Norbert; PAGE, Lee William; BUCK, Ildiko Maria; DAY, James Edward Harvey; HOWARD, Steven; SAXTY, Gordon; MURRAY, Christopher William; WO2014/60770; (2014); 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.956010-87-0, name is 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine, molecular formula is C7H4F3N3, molecular weight is 187.12, as common compound, the synthetic route is as follows.Formula: C7H4F3N3

Step b) 1H-Pyrazolo[3,4-b]pyridine-3-carbonitrile In 33% strength aqueous ammonia solution (10 ml), 3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine (500 mg, 2.67 mmol) is heated in the microwave at 140 C. for 10 min. The mixture is then concentrated under reduced pressure, and the residue is triturated at 70 C. with 100 ml of ethyl acetate and 20 ml of tert-butyl methyl ether. Insoluble components are filtered off with suction in the heat, and the filtrate is concentrated. Drying gives 346 mg (90% of theory) of the title compound as light-beige crystals. 1H-NMR (400 MHz, DMSO-d6): delta=7.47 (dd, J=8.2, 4.5 Hz, 1H), 8.46 (dd, J=8.2, 1.5 Hz, 1H), 8.73 (dd, J=4.5, 1.5 Hz, 1H), 15.02 (br. s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,956010-87-0, 3-(Trifluoromethyl)-1H-pyrazolo[3,4-b]pyridine, and friends who are interested can also refer to it.

Reference:
Patent; BAYER HEALTHCARE AG; US2010/4235; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 393-55-5, 2-Fluoronicotinic acid, 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, category: pyridine-derivatives, blongs to pyridine-derivatives compound. category: pyridine-derivatives

Weigh 10 g (70.87 mmol) of 2-fluoronicotinic acid in 330 mL of anhydrous tetrahydrofuran and stir overnight in an ice bath. A small portion is slowly added with 4.3 g (113.07 mmol) of LiA1H4 to generate a large amount of bubbles. As the amount of LiAlH4 added increases, The reaction solution was yellow and turbid with white turbidity. After the addition, the reaction was continued for 2omin. TLC monitored the reaction. The reaction was completely quenched by slowly adding 10.6 mL of water to generate a large amount of bubbles and solids. The filtrate was filtered off and the solvent was evaporated under reduced pressure to give a yellow liquid. 7.78g, ready for use.

The synthetic route of 393-55-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Chinese People’s Liberation Army Military Academy Of Medical Sciences Poison Pharmaceutical Institute; Li Song; Zheng Zhibing; Lin Feng; Gong Zehui; Lu Xinqiang; Zhou Xinbo; Zhong Wu; Xiao Junhai; Xie Yunde; Li Xingzhou; Wang Xiaokui; (24 pag.)CN107964011; (2018); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 58553-48-3 ,Some common heterocyclic compound, 58553-48-3, molecular formula is C7H6N2O, 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.

1.04 g (8.2 mmol) [OXALYLCHLORIDE] are dissolved in 8 ml dichloromethane. [AT-78C,] 1.28 g (16.4 mmol) dimethylsulfoxide are added dropwise. The solution is stirred at [- 78C] for 20 minutes, then 1 g (7.46 mmol) of the compound of Example 5A, dissolved in 7 ml dichloromethane, is added, and stirring at-78C is continued for another 2 hours. 3.4 g (33.6 mmol) triethylamine are then added dropwise, and after warming up to room temperature, the mixture is purified by column chromatography (silica, eluent cyclohexane to cyclohexane/ethyl acetate 2: 1). Yield: 0.76 g (77% ofth.) Analytical data: see above

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. 58553-48-3, 5-(Hydroxymethyl)picolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER HEALTHCARE AG; WO2004/24700; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 55876-82-9, 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. 55876-82-9, name is Ethyl 5-methylpicolinate. A new synthetic method of this compound is introduced below.

To a solution of methyl 5-methylpyridine-2-carboxylate [Example 2, Step 1] (3 g, 18.3 mmol, 1.00 equiv) in ethanol (20 mL) and tetrahydrofuran (20 mL) was added CaCl2 (8.125 g, 549 mmol 4.00 equiv) and NaBH4 (1.38 g, 36.6 mmol, 2.00 equiv). The resulting solution was stirred overnight at 50 C. The solids were filtered out. The filtrate was concentrated under vacuum. The resulting solution was diluted with ethyl acetate (50 mL). The solids were filtered out. The filtrate was concentrated under vacuum to afford 2.6 g (88.9%) of (5-methylpyridin-2-yl)methanol as light yellow oil. LC-MS: m/z=124[M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,55876-82-9, Ethyl 5-methylpicolinate, and friends who are interested can also refer to it.

Reference:
Patent; Auspex Pharmaceuticals, Inc.; ZHANG, Chengzhi; (94 pag.)US2018/79742; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 134363-45-4, 2-(Pyridin-3-yl)benzoic acid, 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, HPLC of Formula: C12H9NO2, blongs to pyridine-derivatives compound. HPLC of Formula: C12H9NO2

To a solution of 4-(4-Amino-2-fluoro-phenyl)-piperazine-1 -carboxylic acid te/t-butyl ester (1.00 g, 3.4 mmol) and 2-pyhd-3-yl benzoic acid (0.70 g, 3.7 mmol) in DMF (10 ml_) was added HATU (1.42 g, 3.7 mmol) and diisopropylamine (0.65 ml_, 3.7 mmol). After stirring at room tempertaure for 18 h, the reaction mixture was diluted with EtOAc (100 ml_) and washed with H2O (4×50 ml_). The organic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure. Chromatography of the resulting residue (SiO2: EtOAc:Hex) yielded 4-[2-fluoro-4-(2-pyridin-3-yl- benzoylamino)-phenyl]-piperazine-1 -carboxylic acid te/t-butyl ester which was further dissolved in MeOH (20 ml_) and 4N HCI in dioxanes. After stirring for 5 h, the reaction mixture was concentrated down, neutralized with 1 N NaOH, and extracted with EtOAc (3x75ml_). The organic extracts were combined, dried (Na2SO4), and the solvent was evaporated under reduced pressure to yield the title compound.MS: mass calcd. for C22H21FN4O, 376.17; m/z found, 378.4 [M+H]+

The synthetic route of 134363-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; WO2009/6185; (2009); 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

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