Day: March 9, 2021

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.17368-12-6, name is 2-Chloro-4-hydroxypyridine, molecular formula is C5H4ClNO, molecular weight is 129.5444, as common compound, the synthetic route is as follows.SDS of cas: 17368-12-6

A mixture of 2-chloropyridin-4-oi (5 g, 38.7 mmoi), K2C03 (10.7 g, 77.5 mnmol) and iodomethane (10.9 g, 77.5 mmol) in DMF (70 mL) was stirred at RI? for 15 h, diluted with EtOAc (100 mL) and filtered. The filtrate was washed with water, brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo to give the crude product, which was purified bychromatography on silica (5-50% EtOAc in petroleum ether) to give the title compound as an oil. LRMS rn/z (M+FI) 144.0 found, 144.0 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,17368-12-6, 2-Chloro-4-hydroxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; SKUDLAREK, Jason; (79 pag.)WO2016/95204; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 898746-46-8, name is 1H-Pyrrolo[2,3-b]pyridine-6-carbaldehyde, the common compound, a new synthetic route is introduced below. Product Details of 898746-46-8

To a solution of 1H-pyrrolo[2,3-b]pyridine-6-carbaldehyde (196 mg, 1 .26 mmol) in dichloromethane (4 mL) was added, at 0 C, diethylaminosulfur trifluoride ( 260 mI_, 1 .91 mmol). The reaction mixture was stirred 4h at room temperature. Pour the reaction on a mixture of ice and NaHC03 and extract 3 times with DCM. Dry the organic phase on Na2S04 and concentrate the solvents to get 6-(difluoromethyl)-1H-pyrrolo[2,3-b]pyridine XI-1 (96 mg) as a brown solid (1000) Yield: 45%. (1001) Basic LCMS Method 1 (ES+): 169 (M+H)+, 82% purity.

The synthetic route of 898746-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA GMBH; PEGURIER, Cecile; PROVINS, Laurent; CARDENAS, Alvaro; LEDECQ, Marie; MUELLER, Christa E.; HOCKEMEYER, Joerg; EL-TAYEB, Ali; BOSHTA, Nader; RASHED, Mahmoud; (165 pag.)WO2019/243303; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885500-55-0, Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, 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 Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, blongs to pyridine-derivatives compound. Quality Control of Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

General procedure: 5.1.3 Ethyl 4-(cycloheptylamino)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5c) A mixture of 4 (112 mg, 0.50 mmol), cycloheptanamine (76 muL, 0.60 mmol), and Et3N (209 muL, 1.5 mmol) in NMP (3.0 mL) was heated in a microwave reactor at 180 C for 1 h. After cooling to room temperature, the reaction mixture was quenched with water, extracted with EtOAc, dried over MgSO4, and evaporated in vacuo. The crude mixture was purified by column chromatography on silica gel (CHCl3/MeOH = 100:0 to 90:10) to give the product (135 mg, 90%). 5.1.4 Ethyl 4-[(cyclohexylmethyl)amino]-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (5d) Compound 5d was prepared in 62% yield as a white solid by a method similar to that described for 5c. 1H NMR (DMSO-d6) delta 1.01-1.33 (m, 5H), 1.31 (t, J = 7.1 Hz, 3H), 1.61-1.86 (m, 6H), 3.52 (t, J = 6.1 Hz, 2H), 4.26 (q, J = 7.1 Hz, 2H), 6.66 (d, J = 3.6 Hz, 1H), 7.15 (d, J = 3.6 Hz, 1H), 8.53 (s, 1H), 8.81 (t, J = 5.4 Hz, 1H), 11.67 (br s, 1H); MS (ESI) m/z 302 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,885500-55-0, Ethyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Article; Yamagishi, Hiroaki; Shirakami, Shohei; Nakajima, Yutaka; Tanaka, Akira; Takahashi, Fumie; Hamaguchi, Hisao; Hatanaka, Keiko; Moritomo, Ayako; Inami, Masamichi; Higashi, Yasuyuki; Inoue, Takayuki; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4846 – 4859;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 142729-98-4, 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 142729-98-4 as follows.

Example A18; a) Preparation of intermediate and intermediate 57; [Show Image] 4-Cyano-2-pyridinecarboxylic acid ethyl ester (0.090 mol) in MeOH (100 ml) was stirred. NaOCH3 (0.00905 mol) was stirred for one hour at room temperature and the mixture became homogenous. H2N-CN (0.135 mol) was added and the reaction mixture was stirred for 5 hours at room temperature. More NaOCH3 (0.5 equiv) and H2N-CN (0.75 equiv) were added and the reaction mixture was stirred overnight at room temperature. The mixture was filtered. To the filtrate, more NaOCH3 (0.05 equiv) was added and that mixture was stirred for 3 hours and the resulting precipitate was again filtered off. The filtrate was purified by column chromatography over silica gel (eluent: CH2Cl2/MeOH 30/1). The product fractions were collected and the solvent was evaporated, yielding 9 g of intermediate 57 (49%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,142729-98-4, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; EP1904461; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 97509-75-6, 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. 97509-75-6, name is 3-Fluoropicolinonitrile. A new synthetic method of this compound is introduced below.

The mixture of 3-fluoro-pyridine-2-carbonitrile (0.81 g,6.63 mmol) and Pd/C (0.20 g, 10percent wt) in 10 ml of MeOH and2.7 ml of concentrated HC1 was placed under H2 which wasprovided by a balloon and stirred at RT for 4 h, filteredthrough Celite.(R)., condensed, the residue was purified byflash column chromatography, 0.13 g of the titled compoundwas obtained as a light yellowish oil. MS(ES+): 127.1(M+H)+. Calc’d for C6H7PN2 – 126.13.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,97509-75-6, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2006/12374; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 63071-10-3, 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. 63071-10-3, name is (4-Chloropyridin-2-yl)methanol, molecular formula is C6H6ClNO, 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 50-mL round-bottomed flask was dissolved (4-chloropyridin-2-yl)methanol (4.6 g, 32.04 mmol) and tosyl chloride (6.72 g, 35.24 mmol) in DCM (10 mL) to give a colorless solution. To the mixture was added TEA (8.93 mL, 64.08 mmol) and DMAP (0.05 g). The reaction was stirred at RT for 0.5h, and washed with sat NH4CI (20 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to give crude (4-chloropyridin-2-yl)methyl 4- methylbenzenesulfonate. To this product was added methyl 4-hydroxybenzoate (3.07 g, 20.15 mmol), K2CO3 (11.14 g, 80.60 mmol), and MeCN (100 mL). The reaction was stirred at 80 0C for 4h. The solvent was removed under reduced pressure, and to the residue was added water (50 mL) and EtOAc (100 mL). The aqueous layer was extracted with EtOAc (2 X 50 mL), and the combined organic layers were dried (Na2SO4), and concentrated to give crude methyl 4-((4-chloropyridin-2-yl)methoxy)benzoate. To this material was added LiOH (0.828 g, 34.57 mmol) and MeOH (100 mL). The reaction mixture was heated to 70 0C overnight and the solvent was removed under reduced pressure. The residue was diluted with water (50 mL) and concentrated HCl (12N) was added dropwise to adjust the pH to 1. The precipitate was collected by filtration to yield the title compound. 1H NMR (DMSO-ddelta) 65.28 (s, 2 H), 7.14 (d, 2 H), 7.54 (dd, 1 H), 7.66 (d, 1 H), 7.91 (d, 2 H), 8.58 (d, 1 H), 12.69 ( br s, 1 H).

According to the analysis of related databases, 63071-10-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/27746; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 75308-46-2, 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. 75308-46-2, name is tert-Butyl 2,6-dichloroisonicotinate. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloro-isonicotinic acid tert.-butyl ester (3.35 g, 13.5 mmol), Fe(acac)3 (512 mg, 1.45 mmol) and NMP (1.58 g, 16.0 mmol) in THF (400 mL), a solution of methylmagnesium iodide (11.67 g, 70.2 mmol) in THF is slowly added at -77 C. The brown solution turns green-grey. After the addition of about half of the Grignard reagent the dark brown suspension is warmed to it and stirred for 30 min before it is again cooled to -70 C. The other half of the Grignard reagent is added, the mixture turns dark green-brown and is warmed to it and stirred for 16 h. The mixture is cooled to -50 C. and another portion of the Grignard reagent (2.24 g, 13.5 mmol) is added. The reaction mixture is warmed to rt, stirred for 16 h and then carefully quenched with 1 N aq. HCl (100 mL) and diluted with ether. The org. layer is separated and the aq. phase is extracted with ether. The combined org. extracts are dried over MgSO4, filtered and evaporated. The crude product is purified by MPLC on silica gel to give 2,6-dimethylisonicotinic acid tert.-butyl ester (2.37 g) as a pale yellow oil; LC-MS: tR=0.65 min, [M+1]+=208.29.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,75308-46-2, its application will become more common.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2010/63108; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 16110-09-1, 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. 16110-09-1, name is 2,5-Dichloropyridine, molecular formula is C5H3Cl2N, 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.

2,5-Dichloropyridine-4-carboxaldehyde was prepared from 2.5-dichloropyridine using the procedure described in Eur. J. Org. Chem. 2001, 1371-1376 (E. Marzi, A. Bigi, M. Schlosser ) and converted to 2-(2,5-dichloro-pyridin-3-yl)-lH- benzoimidazole using the method in route 1 step 4. This was aminated as described for compound 34 and the aminopyridine converted to compound 38 using the method in route 1 step 1

According to the analysis of related databases, 16110-09-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURIS, INC.; WO2006/50506; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13362-78-2, name is (E)-1,2-Di(pyridin-4-yl)ethene, the common compound, a new synthetic route is introduced below. SDS of cas: 13362-78-2

[Ni(S-mal)(bpe)]¡¤3.5H2O (4) Compound 4 was obtained in similar conditions to 3, but with adding trans-1,2-bis(4-pyridyl)ethylene (0.182 g, 1 mmol). Small green crystals were harvested, washed with methanol and dried in air. Yield 0.040 g (30 percent based on metal). Elemental analysis for [Ni(S-mal)(bpe)]¡¤3.5H2O (NiC16N2H21O8.5): calcd. C 44.0, H 4.9, N 6.4; found C 43.8, H 4.8, N 6.3. Thermogravimetric analysis data. Found solvent weight loss 12 percent (14 percent calculated for 3.5H2O). IR (KBr): nu=553 (m), 612 (w), 686 (w), 832 (m), 974 (w), 1024 (w), 1070 (w), 1219 (w), 1250 (w), 1296 (w), 1424 (s), 1566 (s), 1611 (s), 3368 (m, sh).

The synthetic route of 13362-78-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zavakhina, Marina S.; Samsonenko, Denis G.; Virovets, Alexander V.; Dybtsev, Danil N.; Fedin, Vladimir P.; Journal of Solid State Chemistry; vol. 210; (2014); p. 125 – 129;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 120277-69-2, Adding some certain compound to certain chemical reactions, such as: 120277-69-2, name is 3-Bromo-5-(chloromethyl)pyridine,molecular formula is C6H5BrClN, 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 120277-69-2.

[C] (5-Bromo-pyridin-3-yl)-methylamine 3-Bromo-5-chloromethyl-pyridine (10.3 g, 50 mmol) was dissolved in ammonia methanol solution (7 N, 250 ml) and heated at 60 C. overnight. After aq. NaOH (1N) solution was added to adjust the pH to >12, the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo. The crude product was purified by recrystallization to give title compound as a solid (2.5 g, 27%). MS: 187.1 (M+H+).

According to the analysis of related databases, 120277-69-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; Aebi, Johannes; Amrein, Kurt; Chen, Wenming; Hornsperger, Benoit; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Wang, Zhanguo; Zhou, Mingwei; US2013/143863; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem