Pyridine-derivatives

Application of 934279-60-4, 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. 934279-60-4, name is 2-Chloro-5-(trifluoromethyl)nicotinaldehyde. A new synthetic method of this compound is introduced below.

To a solution of 2-chloro-5-(trifluoromethyl)pyridine-3-carbaldehyde of step 1-1 in ethanol (60 ml) was dropwise added NaBH4 (2.90g, 0.077 mol) while stimng for 30 min at room temperature. After the reaction was terminated with a saturated ammonium solution, extraction with ethylacetate was carried out. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography to give 2-chloro-5-(trifluoromethyl)pyr’idin-3-yl-methanol (12.3g, 76%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,934279-60-4, its application will become more common.

Reference:
Patent; DONG-A ST CO.,LTD; PARK, Jang Hyun; SONG, Seung Hyun; CHUNG, Han Kook; KIM, Heung Jae; LEE, Ji Hye; JANG, Byeong Jun; KIM, Eun Jung; JUNG, Hae Hum; RYU, Chae Lim; HWANG, Jae-Sung; LEE, Hyung Ki; KANG, Kyung Koo; KIM, Soon Hoe; WO2014/157994; (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

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.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

Adding a certain compound to certain chemical reactions, such as: 124236-37-9, Methyl 5-(trifluoromethyl)picolinate, 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, Quality Control of Methyl 5-(trifluoromethyl)picolinate, blongs to pyridine-derivatives compound. Quality Control of Methyl 5-(trifluoromethyl)picolinate

5-trifluoromethyl-2-pyridine carboxylic acid methyl ester (m) (1.03g, 5 . 0mmol) and meta-chloroperoxybenzoic acid (1.2g, 7 . 0mmol) dissolved in dichloromethane (15 ml) stirred at 60 C for 6 hours, to remove the solvent by silica gel column chromatography purification to obtain the product (n) (387 mg, 1 . 8mmol).

The synthetic route of 124236-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Jikai Medical Technology Co., Ltd.; Ge, Yu; (54 pag.)CN105218523; (2016); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1187322-51-5, 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.1187322-51-5, name is 6-Amino-5-iodonicotinonitrile, molecular formula is C6H4IN3, molecular weight is 245.02, as common compound, the synthetic route is as follows.

b) Synthesis of 6-amino-5-(4-fluorophenylethynyl)nicotinonitrile The iodine compound prepared above (300 mg), copper(I) iodide (20 mg) and caesium carbonate (1.7 g) are combined in a three-necked flask and dried at 100 C. in vacuo for 1 h. THF (50 ml), 1-ethyne-4-fluorobenzene (250 mg) and Pd(dppf)2Cl2*CH2Cl2 (78 mg) are subsequently added under nitrogen. The batch is stirred at 100 C., during which a black suspension forms. For work-up, the cooled reaction mixture is added to water and subsequently extracted with ethyl acetate. The organic phase is dried and evaporated. The residue is purified by chromatography, giving 220 mg of the title compound. HPLC [Rt] 3.31 min; [M+H]+238.

The chemical industry reduces the impact on the environment during synthesis 1187322-51-5, I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; Heinrich, Timo; Rohdich, Felix; Esdar, Christina; Krier, Mireille; Greiner, Hartmut; US2015/218155; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 800401-70-1, name is Ethyl 5-bromo-1H-pyrrolo-[2,3-c]-pyridine-2-carboxylate, molecular formula is C10H9BrN2O2, 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. Formula: C10H9BrN2O2

Sodium hydroxide solution (L. lmL, 2M, 2.23mmol) was added to a solution of 5-BROMO-LH-PYRROLO [2,3-c] pyridine-2-carboxylic acid ethyl ester (Preparation 26, 500MG, 1. 86MMOL) in ethanol (20mL), and the reaction mixture heated under reflux for 1. 5h and then concentrated in vacuo. The residue was dissolved in water (15ML) and acidified with acetic acid resulting in formation of a brown precipitate. The solid was collected by filtration and dried to give the title compound as a brown SOLID. AH (d6 DMSO): 7.08 (1H, s), 7.97 (1H, s), 8.60 (1H, s); m/z (ES+) = 241 [M+ H] +.

With the rapid development of chemical substances, we look forward to future research findings about 800401-70-1.

Reference:
Patent; OSI PHARMACEUTICALS, INC.; WO2004/104001; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 62674-71-9, 2-Iodo-6-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, Safety of 2-Iodo-6-methylpyridine, blongs to pyridine-derivatives compound. Safety of 2-Iodo-6-methylpyridine

The title compound was prepared following the procedure reported above for the compound of Example 1 replacing Compound llOa for Compound la and 2-iodo-6-methylpyridine for 3-chlorobenzoyl chloride. After the usual work-up, the reaction crude was purified by automated flash chromatography (SP1® Biotage, 10 g SNAP column) eluting with PE – EtOAc gradient from 9:1 to 6:4 affording the title product as a dense colourless oil (77.8 percent). E/Z mixture 55:45 (1H-NMR).UPLC-MS [M+H]= 353.16, 353.231H NMR (400 MHz, CHLOROFORM-d) mix of isomers oe ppm 7.57 (br s, 2 H), 7.20 – 7.27 (m, 2 H), 7.10 (br d, 2 H), 5.69 (s, 1 H) and 5.62 (s, 1 H), 3.26 – 3.41 (m, 4 H), 2.82 (s, 2 H), 2.59 (br s, 6 H), 2.51 (s, 2 H) and 2.53 (br s,2 H), 2.23 – 2.34 (m, 4 H), 2.21 (m, 2 H) and 1.94 – 2.12 (m, 4 H), 1.62 – 1.81 (m, 4 H), 1.49 (m, 18 H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,62674-71-9, 2-Iodo-6-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; RECORDATI INDUSTRIA CHIMICA E FARMACEUTICA SPA; RIVA, Carlo; GRAZIANI, Davide; LONGHI, Matteo; CALLEGARI, Elisa; FRIGERIO, Fabio; ANGELICO, Patrizia; (197 pag.)WO2019/2571; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 849068-61-7 ,Some common heterocyclic compound, 849068-61-7, molecular formula is C8H5BrN2O2, 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 mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid (20 g, 82.99 mmol) in MeOH (200 mL) was added SOCl2 (30ml) dropwise at room temperature. After addition, the resulting mixture was heated to 70 C and stirred overnight. TLC (EtOAc) showed the reaction was completed. The solvent was removed in vacuo and then aqueous NaHCO3 (20 mL) was added at which time a precipitate formed. The solid was filtered and dried to give methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3- carboxylate (15.3g, 72.3%) as a brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,849068-61-7, its application will become more common.

Reference:
Patent; PFIZER INC.; THORARENSEN, Atli; BROWN, Matthew Frank; CASIMIRO-GARCIA, Agustin; CHE, Ye; FLANAGAN, Mark Edward; GILBERT, Adam Matthew; HAYWARD, Matthew Merrill; TELLIEZ, Jean-Baptiste; UNWALLA, Rayomand Jal; TRUJILLO, John I.; LIANG, Sidney Xi; (212 pag.)WO2016/178110; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 75073-11-9, name is 5-Iodo-6-methylpyridin-2-amine, molecular formula is C6H7IN2, 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. Formula: C6H7IN2

EXAMPLE 255: 6-methyl-5- -(trifluoromethyl)-lH-indazol-4-yl)pyridin-2-amine [0802] To a mixture of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)- lH-indazole (0.05 g, 0.160 mmol), 5-iodo-6-methylpyridin-2-amine (0.025 g, 0.107 mmol) and PdCl2(dppf) (0.012 g, 0.016 mmol) in dioxane (1.5 mL) was added 2N sodium carbonate (0.160 mL, 0.320 mmol). The reaction mixture was heated in a microwave reactor at 130C for 50 minutes. LCMS showed incomplete conversion of the starting material, so the reaction mixture was heated at 130C for an additional 50 minutes. LCMS again showed incomplete conversion. More catalyst was added, and the reaction mixture was again heated at 130C for 50 minutes. The reaction mixture was subsequently filtered through a micro filtration frit, which was rinsed with methanol. The solvents were removed in vacuo. The residue was taken up in DMSO and methanol (1 : 1) and was purified by preparative HPLC, eluting with 25% ACN (containing 0.035% TFA) in H20 (containing 0.05% TFA). The product-containing fractions were dried under vacuum to give a TFA salt of the title compound as a tan film (12 mg, 26%). 1H NMR (400 MHz, DMSO-d6) delta ppm 2.32 (s, 3 H), 6.94 (d, J=9.35 Hz, 1 H), 7.37 (s, 1 H), 7.97 (d, J=8.84 Hz, 1 H), 8.02 (s, 1 H), 8.14 (s, 1 H); ESI-MS m/z [M+H]+ calc’d for Ci4HnF3N4, 293.1; found 293.2

With the rapid development of chemical substances, we look forward to future research findings about 75073-11-9.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; CHERUVALLATH, Zacharia; ERICKSON, Philip; FENG, Jun; KOMANDLA, Mallareddy; LAWSON, John David; MCBRIDE, Christopher; MIURA, Joanne; MURPHY, Sean; TANG, Mingnam; TON-NU, Huong-Thu; WO2013/130855; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem